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Tim Dillon (Comedian): The Boomers Are A Selfish Generation And Gen Z Has Exposed Society's Scam!

Tim Dillon is a comedian, actor, and host of the Tim Dillon Show podcast. In 2017, Rolling Stone magazine named him as one of the top 10 comics you need to know, and in 2022, he released his first Netflix standup special, 'Tim Dillon: A Real Hero’. 00:00 Intro 02:01 I Was a Closeted Gay Addict 03:23 Which One of Your Parents Were Depressed? 07:03 The Impact of Your Parent's Mental Illnesses on You 09:05 Your Parents Divorce 12:32 Childhood Trauma & Taking Drugs 15:51 Hitting Rock Bottom 19:40 AA Meetings 23:15 Trying to Get Sober 24:27 Being a Juror on a Murder Crime 27:41 His First Open Mic Comedy Show 29:25 The Taboos in Comedy 33:20 Why You Don't Get Cancelled 36:09 The Podcasting World 39:42 What’s Up With The Different Generations? 48:09 What Are His Goals in Comedy 49:18 Have You Processed Your Trauma? 55:38 His Experience with Therapy 58:24 Coming Out as Gay & Dating 01:01:50 What Do You Love About Yourself? 01:05:00 Mental Health Coping Mechanisms 01:07:27 Elon Musk Buying Twitter 01:08:35 Social Media Criticism 01:09:46 Touring The World 01:15:03 What Happens in Hollywood? 01:17:40 Rising to the Top: The American Dream 01:20:51 New Generations Don't Work Hard 01:21:49 Remote Working 01:25:05 The Future of AI 01:30:26 Men's Mental Health 01:33:53 Andrew Tate's Influence 01:34:49 Who Should You Have Apologized to and You Didn't? You can purchase tickets to Tim’s new show, ‘American Royalty’, here: https://bit.ly/4aHE6JN You can watch ‘The Tim Dillon Show,’ here: https://bit.ly/3U1DOYp Follow Tim: Twitter - https://bit.ly/49oMOLV Instagram - https://bit.ly/3PPbRRb YouTube - https://bit.ly/3U1DOYp Conversations Cards: https://thediary.com/products/the-conversation-cards-1st-edition Follow me: https://beacons.ai/diaryofaceo Sponsors: Zoe: http://joinzoe.com with an exclusive code CEO10 for 10% off This episode of The Diary Of A CEO was filmed at Gold Tree Studios, located in the heart of the Sunset Strip, West Hollywood, California

Tim DillonguestSteven Bartletthost
Apr 4, 20241h 43mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:002:01

    Intro

    1. TD

      The Zoomers, some of them have figured out that the country's a scam. They invent mental health ailments they don't have, they take days off on end, they terrify their superiors. They found the flaw in the system. They go, "Why are you late?" They go, "I'm gay." You go, "Don't worry about it." Are we still on YouTube? (laughs)

    2. SB

      Tim Dillon! He's a comic icon.

    3. TD

      A master of improv. One of the best in the world. I like making people laugh at stuff that is inherently maybe a little darker because from 13 to 25, I was a closeted gay cocaine addict. But some of our best qualities don't come about because of the best reasons. There's no one better at those random rants.

    4. SB

      Tim, there's a lot of topics I wanna go through with you, and the first is the future of AI.

    5. TD

      We've bred some of the least interesting people on the planet. Influencers, these generic barcodes with feet, those people don't need to exist. They need to be replaced by an AI version of that.

    6. SB

      What's your assessment of different generations?

    7. TD

      Well, we've given up on the children. They're being raised by algorithms. The Boomers, they're the funniest generation, because to be funny you kinda have to just not care, and there's no generation of people that have cared less about the future of this planet, about their children. And then the Millennials were this very ****** generation of, like, want to constantly be patted on the back and told how great they are. "I believe the right things. I tweeted the right thing. I am good."

    8. SB

      (laughs)

    9. TD

      I know that's unpopular, maybe, to say, but I'll just keep going.

    10. SB

      Before this episode starts, I have a small favor to ask from you. Two months ago, 74% of people that watch this channel didn't subscribe. We're now down to 69%. My goal is 50%, so if you've ever liked any of the videos we've posted, if you like this channel, can you do me a quick favor and hit the subscribe button? It helps this channel more than you know, and the bigger the channel gets, as you've seen, the bigger the guests get. Thank you, and enjoy this episode.

  2. 2:013:23

    I Was a Closeted Gay Addict

    1. SB

      Tim, I've watched you for many a year now, and I think you're one of the most exceptional, interesting, provocative, talented comedians, because you have a remarkable ability to (laughs) to, to improvise, it seems.

    2. TD

      Well, thank you.

    3. SB

      And I wonder how someone learns to do that. Where does that talent come from?

    4. TD

      I was a, a closeted gay cocaine addict for many years. Um, you really have to be good on your feet when you are, uh, a closeted gay cocaine addict from, like, 13 to 25. You, you're going to run into situations where you're going to need to, uh, lie, and you're gonna need to be able to kind of, uh, you know, filibuster, and, uh, I guess I got good at it then. I was always good at talking, but I think that was good. That kind of allowed me to think on my feet more than other people would have to, perhaps. Not always for the best reasons. Some of our best qualities don't come about because of the best reasons, but it's good that I have that quality now, I guess.

  3. 3:237:03

    Which One of Your Parents Were Depressed?

    1. SB

      Do you know Jimmy Carr?

    2. TD

      I don't know him personally. I, I, I adore his comedy, and he's, like, um, an amazing comedian, but I don't, I don't know if we've met.

    3. SB

      I was sat here with him two weeks ago, and he said to me, he says, "See, when you meet a comedian, you don't ask a comedian if they're depressed. You ask them which one of their parents is depressed."

    4. TD

      That's a good way to say it, sure. Well, my mother was a schizophrenic, so I tend to think on the mental illness hierarchy, she was kind of, kind of the gold standard, whereas depression, all due respect, is slightly less. Um, and then I think my father might have been on and off depressed, but schizophrenia was the... That was the, um, you know, central challenge in her life.

    5. SB

      For people that don't know what that is or haven't experienced it, what is, how does it sort of manifest, being schizophrenic? Especially for you as a, you know, 10-year-old when you have a schizophrenic parent.

    6. TD

      Yeah. It started to really come out when, when I was about 13, and 12 or 13. Um, uh, it's a lot of paranoia. It's a lot of confusion that as a child you're trying to contextualize. You don't really understand why your mother is talking about people following her or these grand, elaborate, uh, stories that aren't true, and even at 12 or 13 you know they're not true. And you're worried for her because physical illness is very easy to kind of understand as a child, because, you know, somebody's get sick. As a child, you get sick, so you get it. Mental illness is much tougher to understand as a child. You only really start to understand it as you go through life, and when you become more of an adult you start to look back at it because you've had your own mental struggles, you know people that have had mental struggles. At 12 you really don't, for most 12-year-olds, so it's something that I've understood more as I got older, and then it was kind of just very disorienting and confusing.

    7. SB

      And what was the, the sort of cost or the impact that that confusion had, 'cause-

    8. TD

      Yeah.

    9. SB

      ... yeah, you're so right. M- with schizophrenia in particular, when you can compare how your parents are acting to other parents, that sort of disparity or that, like, distinction must be quite-

    10. TD

      It's jarring.

    11. SB

      Yeah.

    12. TD

      It's jarring. When you're young and you are at somebody else's house and you see the way their mother is talking, and you see the way that the family interacts, and in your house when that is different... And my mother was a very fun person, very eccentric, um, a free spirit her whole entire life she had been. It wasn't...... hellish to grow up with her. I, I loved her and she loved me a lot. But around my early teen years, it became apparent that something was wrong. I think I was in the car one day, and I'm remembering she said, "There are people that are following us, but don't worry, they're protecting me." And I found that to be so crazy, like doubly crazy, right? Not only did she believe that there were people following her, but that they were doing it to protect her. I thought that was so crazy. And I remember being young and hearing that, and internalizing that as something is actually really wrong. And I remember thinking about it and telling a friend of mine, like, "I think my mother, you know, is crazy." You know? And, uh, I, I don't under-... You know. And, and that got progressively worse as I got older.

  4. 7:039:05

    The Impact of Your Parent's Mental Illnesses on You

    1. TD

    2. SB

      And what was the impact of all of that on you? Like, growing up in that-

    3. TD

      Yeah.

    4. SB

      ... family home? How does that shape you? And does that leave any sort of fingerprints on you that are still with you today in terms of comedy or who you are?

    5. TD

      Yeah, for sure. Um, the fragility of mental health is something that I understand in a way that other people don't. Um, I understand that people, uh, can have a nervous breakdown, people can, you know, have, uh, you know, a stress-related event that tips them in a direction where... You know, and I've had friends that have had this, right? Like, you know, it's a difficult, uh, thing to understand at 12 or 13. But that was a huge impact on me, uh, growing up, uh, was basically your world is rocked a little bit when someone is suffering from a mental health issue. You feel less secure, less safe. You kind of feel like, uh, something is coming that isn't good. You know, schizophrenia is a degenerative disorder. There is no real cure. There are medifications that can, um, make, uh, the effects less apparent for periods of time. Those medications have really bad physical side effects. So watching my mother go through a lot of, like, physical side effects from those medications, you know, rocking back and forth, right? Uh, uh, muscle twitches and things like that, uh, was also very, was very tough to watch. As, you know, as I got older and, and, and she was medicated, uh, with some very strong drugs to try to like, you know, I guess, uh, mitigate the schizophrenia, it's, it's very tough. It's, it's akin to a loved one getting a physical ailment. It's very similar to that in the sense that, um, you know, you are saying goodbye, in a way, to someone, little by little.

    6. SB

      Mm-hmm.

  5. 9:0512:32

    Your Parents Divorce

    1. SB

      And your father, your, your, your parents divorce around-

    2. TD

      Yes.

    3. SB

      ... this time as well.

    4. TD

      Yeah, yeah.

    5. SB

      And that sort of confounds things, I imagine.

    6. TD

      Yes, I believe that that was an event that probably was, uh, I, uh, I believe she was always a schizophrenic. There was always an underlying predilection for that. I mean, from speaking to doctors, this is what I believe. I believe that the divorce, the stress, that was... But she, she initiated the divorce. I think that was a catalyst for her to feel perhaps vulnerable or, or she... You know, I think a lot of stress brought on kind of the symptoms, 'cause I had never... There were always indications. Uh, she was kind of a, again, a wild person, right? She would go out and collect these Disney toy sets at McDonald's. She would collect Beanie Babies. She would pick up junk on the street and say, "We're gonna fix it up and refurbish it." And, "These are antiques," and everything. There was a lot of compulsive obsess- ob- obsessive kind of behavior. Um, some of the behavior now, you know, a little conspiratorial. I do a joke now though where I talk about it, I go, "You know, the people that are, uh, saying the things that my mother said for years are now, uh, in Congress."

    7. SB

      (laughs)

    8. TD

      So, uh, you know, (laughs) had we known about YouTube, we could've thrown her on there. She would've made a good living.

    9. SB

      (laughs)

    10. TD

      Um, you know, really she would've done well. She was a personable woman. But yeah, I mean, that was, that was tough because he was out of the house, she was there, and she was struggling. And because I'm from an Irish Catholic family, nobody talked about it, and people would use words like eccentric or, "She's fun." They'd be like, "Patty's fun." Nobody would really go, "Wow, I think she's got a real problem."

    11. SB

      And you're sort of 13 years old, so you're going through all of the, you know, the stuff 13-year-olds go through-

    12. TD

      Yes.

    13. SB

      ... figuring out life. You got-

    14. TD

      Yeah.

    15. SB

      ... got any siblings?

    16. TD

      No.

    17. SB

      Okay.

    18. TD

      It's just me.

    19. SB

      Okay.

    20. TD

      Just me.

    21. SB

      That's-

    22. TD

      All the fun for me.

    23. SB

      Yeah.

    24. TD

      Just one. Uh, yeah, it was just me.

    25. SB

      Do you think you were parented from that point onwards, really?

    26. TD

      No. No. I kinda grew up... And it's the generation to a degree as well. I think I'm more of an extreme case because my mother cared about me and she wanted, you know... She hated drugs and alcohol. She hated cigarettes. She hated all these things that if, you know... She would, you know, find a thing, she would go nuts and scream. She was never, like, a permissive person. She did not encourage any of my behaviors. She always wanted me to succeed, and she was always very, you know, critical of, of my behavior. So there was that sense. There was parenting in that sense, where it wasn't a free-for-all, right? But generationally, you know, we just weren't parented the way kids today are parented. There were no cellphones. There was no, uh, you know, "Where is your location?" Nobody was being tracked. You were able to spend hours on your bike riding around the suburbs with your friends. You had a curfew, you had to be in by curfew. You had to make sure that your eyes weren't bloodshot when you went home, because, you know, you were smoking weed for the en- entire time you were gone. Um, so there were things like that.... but in addition to that, which is a kind of a generational difference in parenting, there was just the idea that she was dealing with her own issues. My father was out of the picture, so I had this freedom where it's kinda like I kind of raised myself in a weird way.

  6. 12:3215:51

    Childhood Trauma & Taking Drugs

    1. SB

      A lot of freedom and a lot of trauma, by the sounds of it.

    2. TD

      Yes. Yes. Yeah. There was a lot, I would say, um, unprocessed for a long time.

    3. SB

      And that tends to find an avenue, unprocessed trauma, right? It's-

    4. TD

      It tends to find an avenue. For many years it was drugs. That was the avenue, which is where a lot of it goes, you know? Um, and then-

    5. SB

      How old were you when you started drugs?

    6. TD

      I was... I started smoking weed in eighth grade and, uh, seventh, seventh grade. The summer between seventh grade and eighth grade, uh, I st- I smoked weed a few times in seventh grade, and the summer between seventh and eighth grade, I r- we really ramped it up. We really, you know? Um, I was friends with a, a girl in my town who was fun. She was, uh, a lesbian who rollerbladed everywhere, uh, which I thought was an interesting archetype, and I still do. Uh, and she always was smoking weed while she rollerbladed, and I thought it was a very cool, you know... She was kind of a goth lesbian who smoked weed and just kind of... Very London, to be honest. And she would just kind of rollerblade places, high all the time, and I just became friends with her and I said, "This seems like a good way to live." And, uh, I just, you know, started smoking weed with her. And then very quickly, you know, within a year that, you know, we were doing blow and acid. You know, I dropped acid on stage at my eighth grade graduation, uh, you know, with her and, and another buddy of mine. We'd, you know, drop, drop tabs of acid. Uh, we were doing ecstasy, we were, uh, doing lines of Special K. It was a good time, you know? I mean, this was obviously a response to everything I just talked about. But, you know, drugs are a lot of fun. They have a lot of negatives, but they... That period of my life was, was a lot of fun and terrible. But, you know, that's why I haven't done any of... any drugs or had a drink in 14 years, so I'm not advising it. It's not a course of action I advise. But looking back at it, there, you know, there were certainly good times. I know that's unpopular maybe to say. I don't think that... You know, it wasn't all terrible, is my point. But don't do it. But... You know what I mean? But I wouldn't have traded those (laughs) moments for anything, but it's not a good thing to do. I would've rathered me like a hot surfer or have gotten into sports or something.

    7. SB

      What about... W- w- were you comedic at that age?

    8. TD

      Probably, yeah. I was always kind of a goofball.

    9. SB

      So pe- were pe- were people telling you at that age that you were funny?

    10. TD

      Yes. I would like to make people laugh. I, you know, would imitate... Uh, we had a teacher who died. She was a smoker, and she died of lung cancer, and she had a voice like this and I would imitate her in the back of class, uh, and I would be like, "I'm her3 and I'm fr- in hell now and because of you," you know, things like that. Um, and I would, I would just... We would, you know... It was always kinda like, we'd drive around Long Island and we'd smoke marijuana in cars and I would point at big houses. That's kind of a lot of what we did. You know, we'd drive around, like, rich areas because no one was ever home. No one's ever home in these rich areas, by the way. It's a real... You know, that's just something your audience can take with them.

    11. SB

      (laughs)

    12. TD

      Rich people don't... They're never home. So we would just smoke pot and, you know, drive around, and then I would just try to be funny, and sometimes I would be funny and sometimes I guess I would be annoying. But I was always trying

  7. 15:5119:40

    Hitting Rock Bottom

    1. TD

      to be funny.

    2. SB

      What was the, um, the age range of drug usage in te- and was there a-

    3. TD

      Yeah.

    4. SB

      ... a, a rock bottom? I was gonna say a peak, but it actually goes the other way when it, we talk about drugs, isn't it?

    5. TD

      Yes. So the rock bottom was I was 25. I owned a house that I had bought with a subprime mortgage in a town called Baldwin, New York, and I was an alcoholic. I had not come out of the closet. I had not done any kind of standup comedy. I was working at a mortgage bank in Long Island several years after the mortgage, uh, um, industry had completely collapsed. There was really nothing to do. It was an incredibly depressing place. I worked next to a guy who, uh, was kind of losing his mind. He was just... He was losing his house but he was ordering koi fish for a pond. He wanted to have a nice koi pond and he would spend the majority of the day... His wife would call and scream at him, "We have nothing, we're gonna die," and he would always just call people and he'd go, "What, what size are the fish? And how many of the fish can I get?" You know, so everybody was kind of losing their mind at that point in, in this particular very bleak office, um, you know, kind of industrial park in Long Island, and I was just sitting there trying to be a, a billionaire in real estate, I guess. And, uh, I was hanging out with my friend's father, who's, who's passed away, but he was a really fun guy. Um, he was such a fun guy I was in two boating accidents with him. That's how fun he was. Most people tap out after one boating accident. I was in two boating accidents with this man. Um, he had three DWIs and a BWI. A BWI is boating while intoxicated. It's incredibly difficult to get a boating while intoxicated. It's an actual accomplishment. He was a fun guy. He never had a job his whole life. He sold drugs, um, and his wife worked, and I was friends with his son, I went to high school with his son, but this guy was so much fun, I, we adored him. There was one time me and my friend were sitting at a bar, it was an outdoor bar in Long Island, you know, that kind of dumb tiki bar vibe, and his father came up to us, just me and my friend and a few, uh, girls that we were friends with, and he said, um, "I want, I want you guys," like, "I'm gonna buy all your drinks." And we said, "Okay, thanks," then he walked to the bartender, he pointed at us, he pointed at himself, the bartender thumbs up, we gave him the thumbs up, we said okay. We never got the drinks, we forgot. About an hour later, we got a tab that was like $2,500. We go, "What, what the hell is going on?"And the bartender said, "You just, you agreed to pay that man's tab. He pointed at you, you said thumbs up. He's been drinking here for two days, he has no money." That's the type of guy he was, right? He was just a fun guy. I mean, you know, so we would go fr- o- o- out on Long Island from bar to bar in his little boat. He had, like, this little, little, uh, cigarette boat, like, a real little, you know. And we'd go from bar to bar to bar. And one time, I was 24 years old, we, we were going really fast, it was late at night, and we just ran up on, like, a marsh and we were both thrown out of the boat. And I, like, I literally came to in, like, a nest of egrets, that bird. Uh, those big white birds that...

    6. SB

      Mm-hmm.

    7. TD

      And, and I was just in the middle of the... And I felt to myse- I said, "My life is kind of out of control." That was the rock bottom. That was kind of the, where I said to myself, I said, "You know what this is?" I could have been paralyzed, I could have been killed. I'm like, "This is probably not gonna end well if I keep drinking." So I was laying in that egret's nest at probably 1:00 in the morning in the middle, uh, of (laughs) , you know, the Long Island sound or wherever I was. I think we were in the ocean, we were on, we were in Freeport. And, uh, I was just basically going like, "This is a real problem." So then I went to, to AA. You know, I started, I, I was like, "This is, this is probably time to, like,

  8. 19:4023:15

    AA Meetings

    1. TD

      fix this."

    2. SB

      So you made the decision to go to AA?

    3. TD

      Yeah. I-

    4. SB

      I'm trying to figure out how you get from that egret's nest...

    5. TD

      Yeah.

    6. SB

      ... to that first AA session. 'Cause it doesn't seem like one just wakes up the next day and goes, "Okay, I'm gonna go to AA."

    7. TD

      Well, I, it wasn't the next day. But I, I woke up and what, what basically happened was I, I was around a lot of really, uh, l- e- end-stage alcoholics, meaning, like, these people had drank their entire lives. I was hanging at this bar called Lisa's Lounge, which was a bar in Long Island. It was in the town I lived in, and up the block from the house that was foreclosed was this bar, I could walk to it. It was named, I kid you not, after a woman who died in a drunk driving accident. Her father had named the bar after her. She had died, she was hit by a drunk driver, and he named a bar after her. And people would to- and she... Her picture was on the... I mean, this is unreal, this is true. Her picture was on the wall of the bar and people would toast her, "To Lisa," and everybody would get dr- it was a, it was a, it was a great community of people. And it was a lot of drugs and alcohol, and people that had, uh, you know, nowhere to go, nowhere to go. Like, the, the owner told me once, he goes... As people doing coke at the pool table. He goes, "I, I opened this bar..." I swear to God he said this. He goes, "I opened this bar because I really wanted people that didn't have a place to go to have somewhere to go on Christmas." And then he just did a line of cocaine. And I said, "Well, that's a nice thing." At 24 years old, I thought that was a great thing. Um, and I was just, like, hanging out in this old man bar. This was not a fun bar. This is not where you'd go to get laid. This was not a club. This was not... This was the end. The end. A l- late stage alcoholism. After decades, people found themselves here. And it was so close to my house, I went there. And, um, that was, you know, that was a weight every night when I went to bed. I, I looked at their lives and I said, "I'm young, but this is where I'm going. This is where I'm heading." I had that example, kinda right in front of me. And that, together with my friend's father, together with that accident, started to basically, I said, "I've gotta make a choice now or this is where I'm going," which seemed a little bit worse than death, sitting there in a bar every night, being afraid of who I was, being afraid of trying something in life that I loved, trying to make something of myself. Sitting in that bar, drinking my life away felt like a, a huge failure. I didn't wanna fail. So that's why I stopped.

    8. SB

      There was still something in you. There was still some kind of desire or fight in you, which isn't always there for some people who are in sort of that late-stage addiction. There was some reason to persist, right?

    9. TD

      Yes. Well, I thought that I could have a better life. And that's all you need, I think. And I think that that is the primary motivating factor for anyone to change anything in their life is that they have the hope or the idea, they have the imagination that they can have a better life, if you can conceive of a better life. So I said, "There's probably a version of me that's not drunk every day, that's not working at a dead-end job, that's doing something that he likes." And it was tough. It's not hard to change. It's very difficult to change anything. But that was, that was my, you know, moment where I had that

  9. 23:1524:27

    Trying to Get Sober

    1. TD

      realization.

    2. SB

      Did you know what that better life looked like specifically, or did you just know that it existed?

    3. TD

      Well, I, I knew that it was sobriety. So I knew that it was being sober. I, I didn't have a roadmap for exactly what it would be, but I knew that it wouldn't involve sitting at a bar getting drunk next to someone named Marge, you know, for example, right? I knew that it would be sobriety. I knew that it would be honesty. And those two things go hand in hand. So that was what I knew. And I, and I'd always wanted... You know, as an actor, as a little kid, right? From six years old to 13, to 12, I acted. I was in theater, I was in plays, I was in Sesame Street, on, on the show Sesame Street a few times. I toured around the country in sixth grade with my mother right before the divorce, right before the onset of her symptoms, um, with a, a Broadway show, Annie Get Your Gun. I, I was an actor. I, I liked performing. I enjoyed that life. I'd given up to do drugs when I was, like, 13. But then when I sobered up around 25, about exactly 25, I went to a standup comedy open mic, and that, that was the thing that kinda pivoted the direction of my

  10. 24:2727:41

    Being a Juror on a Murder Crime

    1. TD

      life.

    2. SB

      So does this all happen around the same time? The AA-

    3. TD

      Yes.

    4. SB

      ... meeting, the first standup comedy-

    5. TD

      Yes.

    6. SB

      The AA thing in particular, was that difficult for you? Because I, I kind of understand the 12-step program.

    7. TD

      Yeah.

    8. SB

      And there's some quite challenging elements of that.

    9. TD

      100%. I was also, around this time, a juror on a murder trial. This is something that I shouldn't leave out, 'cause this really did impact me as well. There was a murder trial in Long Island that was pretty, uh, uh, well known. Uh, it was unknown to me at the time I was selected, but a- a guy had murdered, uh, the mother of his children, and he was an informant for the police, and they had failed to follow up on many orders of protection, uh, that this woman had against him because he was providing them information. They, uh, subsequently, after the verdict, settled an $8 million lawsuit with her family, paid, paid her $8 million. So this was like, a pretty big case. It involved police, you know, malfeasance and things like that. Um, and I was selected as a juror, and I really wanted to be a juror on this case because I was bored in my life, and I thought that maybe it would be interesting to be a juror on a murder trial. You know, I thought it was gonna be something stupid like someone fell in a Wendy's and won it, $100,000. But I heard it was murder one, you know, and I'm like, "Well that's fun." You sit there every day, and every day it's just mortality is, is the theme of every single day. Life, her life, his life, his life being taken, you know, him losing his freedom, her life being taken. And that really kind of impacted me too, because I was, you know, going to bars every night, drinking after that, thinking about life and going, "I'm on a, a really bad course, and I gotta change." And A, it was tough. It was difficult, because it's hard to be vulnerable. Like as a comedian, you hide behind the jokes and the bits and things like that, but in that room, you can't do that, so that is difficult. The God thing was difficult, the higher power. I had to come to that in a, in a different way. There's, there are challenges. You know, being honest is a, was a big challenge. I was like, "God." They're like, "You have to be honest." And I'm like, "Okay, I can stop drinking, I can stop using drugs. I don't know if I could be honest. That seems insane. Look at the world we live in. Why would anyone be honest? That doesn't seem to get you anywhere." And they were like, "Yeah, but if you are, become a liar, and you're a compulsive liar, you will go back to drinking and drugs. That's the way it works." So that was the toughest thing for me.

    10. SB

      And you had to forgive...

    11. TD

      Yourself. You have to forgive yourself. You have to forgive, uh, other people. You have to make an inventory of people you've wronged. You have to go to those people and say, "I apologize for what I've done, for taking money from your drawer and using it on drugs, for lying to you, for making you worry about me." These are all important things, and you have to do it, and it's, it's really hard to do, but it's important to get over that hump.

  11. 27:4129:25

    His First Open Mic Comedy Show

    1. TD

    2. SB

      That first standup gig-

    3. TD

      Yeah.

    4. SB

      ... that you do-

    5. TD

      Yeah.

    6. SB

      ... how did you get on?

    7. TD

      It was an open mic, and it was, uh, at a coffee shop in Long Island, in, in a place called Merrick.

    8. SB

      Yeah. You were sort of 25 years old, 25 at the time.

    9. TD

      I was 25, and it was also a tattoo shop, so you would hear like, tattoo needles as you, if you weren't doing well it would, "Zzz." And it would just be guys having, you know, having their girlfriends' like, tattoos like, changed, because they were no longer in the relationship. So they were like, they were making them into missiles and like, patriotic things or 9/11 remembrances, you know, whatever the case may be. And occasionally, they would chuckle, and then there was a few like, local people that liked comedy that would come to the coffee house. Um, but it was kind of an everybody gets on thing. So that's the beginning of comedy is like, everyone gets on. It's an open mic. You just go and you're on.

    10. SB

      And it went well?

    11. TD

      It went as well as it could've gone for the first time. I got some laughs. Certain things d- didn't hit, but I felt confident and I felt like I belonged and I felt like I was doing the right thing. And I, for the first time in my life, was like, I, I felt kind of certain that I would keep doing this. There was a certainty, and for the majority of my life, I wasn't certain of anything. I was kind of trying different identities out, trying things out, seeing what would work, and then this, this was like, "Okay, this was, I'm good at this. I can get better at it, and I like it enough to work hard at it."

  12. 29:2533:20

    The Taboos in Comedy

    1. TD

    2. SB

      Comedy. Comedy's, um, comedy's in an interesting time, it appears, as someone that's not, uh, at all involved in comedy at all. Because you have these like, for- these two forces almost colliding, more so than I've really ever seen in my lifetime, which is-

    3. TD

      Good and evil. No, I'm kidding. (laughs)

    4. SB

      (laughs)

    5. TD

      Hello.

    6. SB

      No, but it's like, correctness and comedy-

    7. TD

      Yeah.

    8. SB

      ... are at war...

    9. TD

      (sighs)

    10. SB

      ... it seems.

    11. TD

      (sighs) Sure. Well...

    12. SB

      And even correctness has now-

    13. TD

      Yeah.

    14. SB

      ... made its way onto the stage of comedy.

    15. TD

      Yeah. I, I think that there is always going to be taboo subjects. There's always gonna be things that are harder to make funny than other things. There's always going to be a line. As George Carlin said, "Your job is to find out where the line is, cross it." You know? You gotta get good at stuff to make people laugh at stuff. I like making people laugh at stuff that is inherently maybe a little darker, 'cause of the way I grew up, but I gotta make sure those jokes are funny enough so that people will laugh at them. And then there's some people that will never laugh at them.... there's some people that don't understand comedy, they take it very literally, they don't like it, they like to be bothered by it. They get angry about it. They're unhappy about it. Someone's making someone laugh somewhere and they're angry. I don't know what to do with those people, I don't know how much we can pay attention to those people. I know many of them write articles and, you know, uh, you know, uh, eh, the monologue on television about that they're upset about something, I just don't know, uh, how much attention we've paid. We've paid a lot of attention to them over the last four years. I think people are a bit exhausted by it, I think people are a bit over it, I think there are people in society that they, they're allowed to have their reactions to anything you do. You're allowed to hate me, find something I've said offensive, disagree with me, you can write about it, talk about it, whatever you wanna do, I, e- it's really kinda not my business and there's only so much attention that I could pay to it. I think that's kind of the way comedians have to look at this stuff. They go like, "Hey man, w- we're, we're making jokes, we're having fun." You have the right to be very angry about it and be upset about it, but, I mean, again, that's a little crazy, in my estimation, to be that upset, uh, by comedians that have no real power. The thing about comedians, we don't ha- but now people say, "Well, you have cultural power, soft power," whatever, that's, sure, but we don't have (laughs) the type of power that CEOs of large companies do. Our job is not to, you know, move a conversation forward, our job is not to... It's j- our job is to be funny. Now, if we do s- th- some other things, if we happen to shed light on something that's good, if we move a conversation forward, if we illustrate a truth, that's a great thing and it's secondary. Our primary job is to be funny, and that can be that's being wrong, that's being stupid, that's being shortsighted, it might be even being bigoted, if it's funny. Eh, w- we're not in the, we're not in the job of being right. We're not in the job of being correct. There are people whose jobs are, they have to be right. A surgeon has to be right. They can't just wing it. We are in the job of being funny so if you confuse those things, which a lot of people out there do, that's where you get this tension, you know? But again, I'm a clown, I perform at comedy clubs and theaters, I do a podcast, if I say something you don't like, there's, it's really, really an infinitesimal chance that anything I say is really going to have the gravity and weight that these people think it does. Um, you wanna be looking at other people that have more power. Direct that energy somewhere else.

  13. 33:2036:09

    Why You Don't Get Cancelled

    1. TD

    2. SB

      You say direct that energy somewhere else, but I watched that video of you getting, um, (clears throat) very irate because-

    3. TD

      Yeah.

    4. SB

      ... Rogan, uh-

    5. TD

      Yeah.

    6. SB

      ... he gets canceled and you don't, and you say some pretty amaze-

    7. TD

      Yes, I'm trying to get canceled, yes.

    8. SB

      (laughs) Yeah. You seem uncancelable in many respects.

    9. TD

      Well, no, no, no, I'm not uncancelable. I'm a goofball. I wear crazy glasses, I'm a comedian, I say things that probably are intelligent, and sometimes people will look at me and go, "That's a good take." A lot of the things I say are completely absurd. Um, and n- m- I, you know, I don't even know which is which when I say it, because I do two hours of broadcasting, I've done it for eight years and I don't know what I'm going to say until I sit down and I talk. And some of the things I say that are absurd start intelligently, and some of the things I say that are intelligent maybe start absurdly, and that's the fun of it to me. If I knew what I was gonna say or if I had an agenda if I wanted to say a certain thing, I would get very bored very quickly, but I just try to look at stuff and go, "What do I think? What do I think? I'm being told this, you know, what, what's my reaction," you know?

    10. SB

      Mm-hmm.

    11. TD

      And that's kinda like what I try to do. But yeah, I think I'm, I'm goofy and if people are mad at me, they're kind of, they're, they look stupid sometimes because of how over the top I am about certain things and how wild and, and again, a lot of it I think is funny, right? So Joe has a different podcast, he has like a, he has a podcast where it's, sometimes it's funny but he has very serious people on, he has the biggest podcast, I think in the world. I think you guys are maybe the second, right? Are, you're up there?

    12. SB

      I have no idea.

    13. TD

      You have no idea? Okay, clever.

    14. SB

      (laughs)

    15. TD

      But, you know, like, he's hugely successful and he, you know, does all these really amazing interviews where he researches and he reads books and he's smart and he's talking to somebody and I'm, like, shooting from the hip. I'm just going off the top of my head and, like, halfway through a story I'll go, "Oh, no," and I'll just go the other way on it because I'll realize, I'll r- sometimes I'll read the third paragraph, I'll be dismissing the whole thing and then when I get to the third paragraph, I go, "Oh, this is a problem."

    16. SB

      (laughs)

    17. TD

      So it, it is, and that's what I think makes it funny.

    18. SB

      Joe Rogan?

    19. TD

      Yeah.

    20. SB

      Um, y- going on his show, you, you describe that as being really pivotal in your career.

    21. TD

      Yeah. He's the most generous person that I've met with his audience, with his fanbase, all he wants is other people to succeed. He brings on comedians, he brings on writers, he brings on journalists, he helps them promote whatever they're doing, he has this huge fanbase, he shares it with people, so I'm very lucky that he's had me on his show a bunch of times. And he's a very good friend and, like, when I go on his show, we just have the conversation that we would have privately, we have it on his show. So I think that's why people

  14. 36:0939:42

    The Podcasting World

    1. TD

      like him.

    2. SB

      Podcasting.

    3. TD

      Yeah.

    4. SB

      It's, uh, I mean, it's taken on a life of its own. What do you think of podcasting? I mean, it's been on a bit of a journey.

    5. TD

      Yeah.

    6. SB

      Obviously there's, um, there was this big... I think podcasting was like the OGs of podcasting, like Rogan started out and then-

    7. TD

      Adam Carolla, Joe Rogan-

    8. SB

      Y- yeah, and then there's this-

    9. TD

      ... Keith and The Girl, a show in New York City, uh, Marc Maron, those guys were in the very, very early...

    10. SB

      Before it was cool, before anyone was really like-

    11. TD

      Yeah.

    12. SB

      ... before the money was there.

    13. TD

      That's right.

    14. SB

      And then the celebrities show up. It was like a bit of an experiment for a couple of years. It seems Spotify have kind of roll back from that experiment.

    15. TD

      Yes, because they have nothing to say. Um, most celebrities don't. A lot of them, uh, uh, you know, are invented people who are created in a laboratory, and the laboratory is CAA, uh, my agency (laughs) -

    16. SB

      (laughs)

    17. TD

      And, uh, and they create a person and they get, um, uh, public relations people, they get lawyers, they get, uh, all these people, business managers-

    18. SB

      (laughs)

    19. TD

      ... agents. They come in and they go, "This is who you are. This is what plays. These are the things you highlight about your past. These are the things we don't talk about. Let's leave the Confederate flag at home." You know, they create a person. That person then goes and they're now famous. Um, it's a terrible idea to give that person a microphone and tell them to talk for an hour. It's terrible. You know, many of these people aren't that talented. Some of them are, some of them are amazingly talented. Some of them are ve- very kind of banal people. People tend to think of Hollywood as this place where it's all satanic pedophiles eating children. Now, undoubtedly, some of that is true, but a lot of it is just very banal, boring people that have been created by these corporations that, uh, when you realize how boring they are, and then you look at how much money they have and where they live, that's what will drive you nut- you'll go, "Oh my God." So that's why podcasting is a really, really bad idea for these people. They should be kept somewhere. They should have very managed, uh, things where they come out on the red carpet and they go, "Uh, how are you doing?" And they just go, "Climate change," and then walk into the auditorium and get an award. They should be allowed to speak two to three words at once, and they should know what those words are beforehand. Um, it is a terrible idea to give someone... Again, the, these people that all of their interactions are with other famous people, all of their thoughts are filtered through a prism of, um, you know, corporate lawyers before they can say anything. Uh, this is not what podcasting is, in, in my estimation.

    20. SB

      Is there any celebrity podcast that you think is-

    21. TD

      I'm sure there's some that are really good. This is not everyone, right? I'm sure there are people that have really good podcasts, but, like, if we're just talking in general about let's give A-list actors a microphone, probably not the best idea. Just probably not the best idea. You know?

    22. SB

      What's your, um-

    23. TD

      'Cause I know they, they gave Meghan Markle money, they gave, they gave a lot of people money there, uh, at Spotify, and, you know? And so I don't know that that... But that, then they came out and said, "We made a mistake. We shouldn't have given these people money."

    24. SB

      Do you think you should've gotten the money instead?

    25. TD

      Of course. I absolutely believe that. But, you know, I, I, I can't compel them to give me the money. I can't compel them. I can't get a member of the royal family to marry me, and I would've stayed in that castle no matter what was said.

    26. SB

      (laughs)

    27. TD

      And, but I can't have that happen, so I can't... You know, Oprah doesn't interview me, so you got... You, you... I have enough money. But the, um... Sure, you know? I th- I think it's... Podcasting, to me, the fun of podcasting is being unfiltered, free, and just having fun.

  15. 39:4248:09

    What’s Up With The Different Generations?

    1. TD

    2. SB

      What's your assessment of these sort of different generations? We have these Gen Zs, Millennials, and we have the Boomers. What's your read on these people?

    3. TD

      Well, we've given up on the children. The future is not the children. Uh, the children are no longer the future. The future is AI. The future is robotics. We're very clear on that. We don't even talk about the children anymore, we talk mainly about AI. No one's even said anything about the children in months, years really. Uh, we've given up on the children, they're dead-eyed little monsters, they're running around killing each other. We can't deal with it. It's very traumatic. I've even stopped thinking about what they're doing 'cause it's crazy. I'm more excited about AI than the children, just like anyone else. Who's reviving the economy of San Francisco? The children? No. AI. So AI is next. We don't know what we're gonna do with the children. Build prisons, that's what I say, for children. Um, they're crazy, um, they're being raised by algorithms, they're all on fentan- all, they're all on drugs, we're all running around trying to kill each other and, and record it. Um, there was a case in Phoenix, Arizona, these rich white kids running around beating up kids at random, filming it and putting it on TikTok. No motive, nothing, just for clout, just for the exci- And they killed a kid, and finally now, 'cause they're all white, of course, the cops didn't do anything for a year, and they were like, "Well ............................ Just a couple of kids having fun killing other kids. This is how people grow up." So this Gilbert Arizona Police Department does nothing about the whole thing. Finally, they just arrested these kids 'cause they, they killed somebody. But this is not only there, I mean, it's kind of an epidemic where, like, all over the place you see, like, you know, young people unfortunately, you know, these crazy acts of violence that are now being uploaded for clout. People going, "Look at what I did," and what they did was like, you know, assault someone or kill someone. This is a real problem. Um, so we have to deal with the kids in some way, jail them, put... I don't know what to do with them. But AI is big, eh- robotics is big. That's what is next. The Boomers, I have a book coming out about them. I love the Boomers. They're a selfish generation, uh, o- of people. It, the, the, the, the state of the Boomers, these, these paranoid people who refuse to leave their McMansions, they will not leave, they will not retire, uh, they lord around their houses, uh, they, they, they, uh, diminish their children. They say, "I can't believe you don't own something like this." They like holding these houses over their kids' heads. Um, they retire to bigger houses, they have thousands and thousands of square feet. They're very sick people. They refuse to give up their jobs, they're dying in the Senate, they're collapsing in Congress. They will not leave, uh, they will not cede any of their power. They are emotional terrorists, uh, and, uh, and I grew up with them and they're very interesting people. They- they've proven the lie of the '60s, these hippies that everybody thought were like progressive, they're actually not. They were always just selfish drug addicts. They never cared about, uh, anything they purported to care about, they just wanted to get high and roll around in the mud.... and then as soon as the drugs changed from, you know, uh, whatever, from, uh, you know, acid to money, uh, they, you know, became this very, like, materialistic, soulless group of people, but the funniest generation that has ever lived. Nobody's funnier. Nobody's funnier, because to be funny, like we talked about, you kinda have to just not care about anything, and there's no generation of people that have cared less about the future of this planet, about their children, about anything, than the boomers. Uh, they're all little islands, and they all are about themselves forever and ever, and there's something actually refreshing about that, funny, um, and they're holding the planet hostage. They won't die. They won't leave. I've suggested they be forcibly evicted from their homes and committed to mental institutions. Legally, we have some problems. That's not easy to do. Um, I've spoken to some lawyers. There are problems doing that. Um, and then the millennials were this very shitty generation of, like, "Pin a me- medal on me, pin a ribbon on me. I'm right. I went to the right college. I got the right internship. I believe the right things. I Tweeted the right thing. I did the right thing. I have all the right beliefs. I have the good politics. I have this. Shower me with... Tell me I'm good, 'cause my boomer parents, they don't care about me, but you tell me I'm good. The world needs to fill the void that exists inside of me." Uh, and these millennials are these kind of ambitious people that, uh, want to constantly be patted on the back and told how great they are, so they're kind of shape-shifters that conform to any popular sentiment. They crowdsource all of their opinions. They just want... Whereas the boomers just kinda didn't care about anyone or anything, you have the millennials who are kind of, like, more like, "I am good, and you tell me that I'm good," because they're not... They're good to be told to be good. Their politics are aesthetic. They want everyone to look at them and to tell them how great they are. And then the zoomers are the younger generation, after the millennials. They seem to be, you know, somewhat, like, they're self-starters. They're very skeptical of institutions. They're a little more cynical. That's some of their positive qualities, that they're more independent-minded. The negative qualities are the aforementioned, um, murder and the filming of the murders, and the killings, and the drugs, and the fentanyl vapes, and all of that. That seems to be less. I mean, we need a draft, to be honest. You know? Now that I'm kind of older and, uh, fat, now we need a draft. Young people should probably just go into the military. I, I, I've, I've... I know that's gonna be a controversial thing to say, but if they're just gonna do fentanyl, and attack each other in malls, and put it on TikTok, they can go die in the Ukraine, so that Boeing can make some money. Are we still on YouTube? (laughs)

    4. SB

      (laughs) So are you, um... Would you consider yourself to be optimistic about the future? There's a lot going on in the world.

    5. TD

      No. No. No, I, I, I, I don't, I don't... I'm, I'm sane, so I don't, I don't... I, I think there's good things happening, but I'm an optimistic... But the future overall? I don't know. That's tough to be. Maybe. Right?

    6. SB

      I mean, you've got, you've got elections coming up this year as well, here in-

    7. TD

      Yes.

    8. SB

      ... the US, which is a big-

    9. TD

      Well, we all know elections solve everything.

    10. SB

      (laughs)

    11. TD

      We all know that's where the real power lies, the elections. No. Yeah.

    12. SB

      When you were talking about refusing to relinquish control and power of the boomer generation, I was thinking a lot about Biden there-

    13. TD

      Sure.

    14. SB

      ... 'cause it seems like your presidents are getting older and older and refusing to...

    15. TD

      Yeah. I mean, Biden seems to be a bit old. Trump's, uh, old. You know, Biden is, seems to be in a, a stage of mental decline now. He was really good at the State of the Union. They gave him something, they shot him up with something, which was great. Uh, we have no new talent in the country. Uh, nobody wants to be a politician anymore unless they're psychotic. You need young people that care about the country, uh, that want to change it, and what you're getting now, more and more, is, you know, all of the interesting people in our country are... And, and the people that are ambitious, and the people that have talent, they don't wanna be in politics. They wanna be somewhere else. It's more fun to go to Miami and trade Bitcoin on a yacht. You know what I mean? They just don't wanna be in politics. They don't wanna do it. So you end up with these octogenarian, uh, drooling, somewhat, uh, you know, like, dementia-ridden elderly people who are incapable of even understanding what's happening in the c-... They don't even know what it i-... They barely know what TikTok is. TikTok is something their grandchild shows them, you know, at some party they're having in Maine. They're sitting on a, on a hill in Maine, eating lobsters falling out of their mouth. They go, "Look, Grandpa, look at the TikTok," and they go, "Aah!" And then they have to then go into Congress and, and hash this out? No, so I mean, the problem really is we just don't have young people that care enough about the country, because the press is gonna rip their lives apart. Right? They're going, "There's so much more money elsewhere. Uh, there's so much more." And the system's so toxic and so corrupt. They go, "I don't wanna get involved in that."

    16. SB

      They're gonna ban TikTok, aren't they? th- they're talking a lot about banning that.

    17. TD

      (laughs) They're talking about it. I have no followers on it, so I'm f- I'm for the ban.

    18. SB

      (laughs)

    19. TD

      You know? Uh, for personal, completely personal reasons, I'm for the ban, and I also think it's a prob... It's... I don't know. I don't know anything about it. I, I just know that people are making a lot of money on it, and so if I say I'm for the ban, people get angry with me. It's not a good... It's not a good cultural force, but what is?

  16. 48:0949:18

    What Are His Goals in Comedy

    1. TD

    2. SB

      Do you have goals? In terms of your comedy and your career more generally, do you have, like, g- stated goals?

    3. TD

      Yeah. I have things I wanna do. I have... You know, the boomer thing, I wanna do a show about boomers. I've always wanted to. The book is gonna be a large part of that. I wanna do either a movie or a show. There's something... I find it very funny the way I grew up. My friends' families, their parents were very funny people. Now, I want to do something that kind of immortalizes that, 'cause they are g- about to leave. They are about to go, and there's something very funny about them, and I wanna make something about... I think a lot of comedians, maybe everyone wants to do something about their childhood or do something about how they grew up, or... But I...... you know, I- mine will be good. That would be the difference. No, I, I really like the idea of that. That's a goal. Just to tell that story is a goal. I'm banging on the desk.

    4. SB

      (laughs)

    5. TD

      I apologize. Um, and then it's just to keep making people laugh and to keep having fun, you know? I mean, all the things that I, I, there's certain... That, that boomer story is something I wanna tell. You gotta find the right platform, the right medium. But that's something I wanna do.

  17. 49:1855:38

    Have You Processed Your Trauma?

    1. TD

    2. SB

      The, um, the, the, all those early experiences that you've had have, have quite clearly manifested in your work in various ways. You talked about the unprocessed trauma from your earliest years.

    3. TD

      Yes.

    4. SB

      Have you processed it?

    5. TD

      No. No, I mean, I, I, I processed some of it. Some of it. I mean, I don't know that I processed all of it. I don't... In, in one lifetime it's a tough thing to process all of it. But I've processed a good amount of it, and I've come to a point where there's always more work to do. You could always be in a better place mentally, and you should try that. Try to get there. Um, but I think I've done a good job of processing it. I lost my mother about six months ago, uh, I think. Or no, it was August. She died in August maybe, maybe six months. Um, and it was a very difficult thing to go through because the r- their whole life was not great at the end. But it was in the beginning. She had a lovely, amazing life in the beginning. Her and my father were married for 10 years before they had me. She loved surfing and boating, and she spent a lot of time in Florida, and she was kinda... She was voted best looking in her high school. She was very, very attractive early on. The front nine were good. The back nine were a little tough. But I had her out to my house, um, on Long Island, and the whole family was kinda there. We had a really nice day of everybody, my cousins, my, her sister, everybody being there, and that was a, a good moment. That's what I'm remembering. And it was... You know, she was as good as she could be. Um, I, I try to get more religious as I get older and more faith... I, I think faith is a good thing to have. Um, you know, obviously religion being a human institution, there's, there's pitfalls. There's problems. You know, we don't have to rehash them. Um, the idea of there being a spiritual realm, to me, is, I think, very interesting. I think it seems to be quite possible. I think that people are more than their bodies. They're more than the flesh. They're more than... There is a spirit there, and I think there was a spirit in my mother that was trapped in a very difficult situation, and I think that spirit is free. And I think that's the way that I feel about a lot of things now, is that I seem to be getting more into this idea of, you know, the physical not being everything, and that we, we should develop a spiritual side of ourselves. And I'm, I, I, I look at the struggles that she had later on in her life, and I was like, "Keeping her in a body and in a mind that is actively fighting against her was a selfish thing. So letting her f- having her be free, I think, is, is the best, you know, outcome."

    6. SB

      It's a complex set of feelings.

    7. TD

      It is.

    8. SB

      Because there's grief on one end and then there's something else on the other, right? There's like a...

    9. TD

      Well, there's relief because she was in pain. So when someone's in pain and they depart, uh, this world, you are... There's a relief that you have because watching them go through that is terrible. It's hard. And this is people that suffer in all kinds of ways. So, you know, again, I think people are more than their bodies and, you know, I think they are... You know, the, the soul, I believe, is a real thing. I believe the spirit is real. And I was raised Catholic. There's parts of C- Catholicism I don't vibe with as much, obviously. The terrible lineage of abuses. Uh, but then there's parts of it that I think are really good. Having a spiritual dimension to your life, I think is really good. So, you know, I, I look at it in... I would never say, like, it was time, but she had suffered greatly for a while, and having her out of the house and having her be with everybody kinda for the last time, nobody knew she was gonna die, but like, that was just kind of a moment where I think she might have felt like it was okay to let go. I don't know if that's true or not.

    10. SB

      Have you, have you been to therapy to process...

    11. TD

      I have. I've been, yeah. I'm not in it currently, um, because I'm on tour, but I... And I haven't been in it in a bit, but I, I certainly have. And I think it can be very good.

    12. SB

      I've been to therapy.

    13. TD

      Yeah. It can also not be good.

    14. SB

      Yeah, it can also be... Yeah.

    15. TD

      It can also not be good.

    16. SB

      Mm-hmm.

    17. TD

      But it can be good.

    18. SB

      'Cause you pre- presumably, you wanna have your own family someday? I'm presuming.

    19. TD

      Perhaps, yeah. I mean, I don't know. I've done, I've done a lot of career stuff for a very long time, and I think at the age I'm at, in your late 30s, you kinda start realizing that there's just a ceiling. Not even career-wise, but in how happy it'll make you. So, my career might get a lot better, uh, but the, the amount of joy you derive from accomplishments as you get older starts to dim, and you actually start enjoying other people's accomplishments. You start looking around. Community makes you happy. Being involved in things makes you happy. Um, helping people makes you happy. It starts to shift. If you are, you know, on a good path, I think you start to shift from like, "Me, me, me, look what I've done," to like, "Hey, can I help somebody?" Or, "Can I be part of something that has a value?"

    20. SB

      What's the, the bigger side of you that your audience don't un- don't understand or don't know?

    21. TD

      Um...

    22. SB

      'Cause I've watched you for years.

    23. TD

      Yeah.

    24. SB

      And I think I've watched a one dimension of you.

    25. TD

      Yes. A funny one, hopefully.

    26. SB

      Yeah, really funny, but I-

    27. TD

      Um, that, you know, I think ev- everyone that they watch, me as well, um, is a human being and not always on all the time. And I think that, you know, there, there's a dimension of me that you get on the show. There's a dimension of a lot of ... and to ... You, you get a lot of what I think on the show. Like, if you went out to dinner with me, I ... and the things that I'm saying on the show are what I would say there. Like, I would ... I'm not gonna have an opinion on the show and then

  18. 55:3858:24

    His Experience with Therapy

    1. TD

      sit down and go, "Well, actually this is the way I really feel." Everything you hear is what I think, and some of it's really funny, some of it's not. Um, but I think it's just, like, just a dimension of, like, being a human being, uh, uh, apart from being a product, right?

    2. SB

      Mm-hmm.

    3. TD

      Where people just consume the things you're saying and doing. A lot of people probably didn't know s- a lot of this. Some of them did, 'cause I'm pretty open about it, but, like, you know, I think that a lot of people just see one side of you where, here's a guy who makes everything funny or tries to make everything funny, but then there are a lot of things too where, you know, I have interests that aren't comedy, I have interested or not, you know, my career, I've interested or not, and I like to, you know, you know, talk about the spirituality stuff. That's probably something that I don't talk about. Maybe I'll bring it up. It's like an aside. But there are interests that I have that are varied, but for whatever reason I'm like, th- it's not funny or it doesn't fit the show that I'm doing. So, there's a show and then there's a person, right?

    4. SB

      Mm-hmm.

    5. TD

      That's not me. That's every entertainer everywhere.

    6. SB

      Your show at the, uh, Royal Albert Hall that's coming up, it's in a couple of days time.

    7. TD

      Yeah.

    8. SB

      Um, one of the things that I am always shocked by with you, and you said it earlier, is that when you do your podcast or when you do these, sort of, long, lon- long form bits, it appears that you're basically freestyling.

    9. TD

      Yeah.

    10. SB

      Uh, uh, w- what's going through your head? Like, I've always wondered.

    11. TD

      Yeah.

    12. SB

      When ... If you're sat on Rogue and if you're sat on your podcast-

    13. TD

      Yeah.

    14. SB

      ... and, you know, your producer pulls up some article-

    15. TD

      Right.

    16. SB

      Do you just kind of trust-

    17. TD

      Yes.

    18. SB

      ... that you'll fi- (laughs)

    19. TD

      I, it's what I used to do when I was a drunk. I would sit at a bar and talk, and now I just do that without alcohol. Like, I, I've l- I, I like looking at things and trying to figure out what's going on and trying to make them funny, and that's the value and the service that I provide, is like, here's a landscape of stories and articles and things, and what the hell's going on? And let, let's see if we can make it funny, and let's see if we can understand it on a deeper level, because there's so ... You know, the press has all these agendas about, like, what they want you to believe all over the place, left-wing, right-wing, whatever, centrist, corporate, just buy things, whatever it is. And what I like to do is look at them and go, "Well, maybe there's a dimension here that's more human that I can flesh out because I'm looking at it and I, I don't have an agenda. I don't care either way. I'm not sponsored by the person in this article. I don't have a alliance or an allegiance to anything." I'm looking at it and going like, "What's the funniest take and how does this, you know, h- how does this explain something larger that's going on?" That's interesting to me. That's fun to me. I like doing that. So, I think it's been successful because I enjoy it.

  19. 58:241:01:50

    Coming Out as Gay & Dating

    1. TD

    2. SB

      You came out as gay at roughly, sort of, 25 years old-

    3. TD

      Yes.

    4. SB

      ... during that period of your time, during that period of your life, um-

    5. TD

      Very late-

    6. SB

      Very late.

    7. TD

      ... by today's standards. Most people, statistically, today come out at the age of two.

    8. SB

      (laughs) You came ... So where do you fit love into all of this?

    9. TD

      You try to fit it as, as, i- in- into it as, as much as you can. You know, you try to ... you gotta ... You know, it's hard because you travel a lot.

    10. SB

      Mm-hmm.

    11. TD

      And it's hard because you are spending a lot of time doing the things that are benefiting you in one part of your life, but sometimes that hurts another part of your life. So you try to ... And again, like, once you start, like, you know, having success it's v- ... So a lot of comics, like, marry other comedians or somebody in that world who gets it, who understands it. So, you know, I think, you know, that's been something I've seen and, and that works a lot of times. Like, people are really happy and bring up great families, kind of, in the world of comedy because their partner gets it. But for me, I, I don't know if that's gonna ... I don't want that, really. I would like somebody who's completely, like, not involved with this at all.

    12. SB

      Are you dating?

    13. TD

      Yes, but not in ... not one person in, like, a serious way.

    14. SB

      (laughs)

    15. TD

      You know? Like, you're just around and, you know, kind of meeting people and seeing, like, what's fun.

    16. SB

      Have you ever been-

    17. TD

      Homosexuality's slightly different.

    18. SB

      Yeah. (laughs)

    19. TD

      So it's not like a whole ... You know what I mean? It's not the royal wedding per se. It's not like moving to the castle, but maybe one day, you know?

    20. SB

      Have you ever been in a long-term relationship, a serious one?

    21. TD

      On and off, but not s- not serious where it's like, again, like, it's gonna lead to marriage and children. There is kind of that difference where, like, you know, not that gay people can't get married and have kids, I mean, they can and have, and blah, blah, blah, we know that, but I personally have not been in a relationship wh- uh, where it was like, "This is where it's going." And I think it's, a lot of it is because I was just so hyper-focused on, like, trying to figure out a way to do this really hard thing, which was, like, be a comedian. But, you know, now I think I'm more open to that stuff because, like I said, you know, you do some stuff, you do some cool stuff, and then you, like, wanna enlarge those other parts of your life that you've neglected.

    22. SB

      I was the same for most of my life, but I actually think when I look back, I just had a ... (sighs) I think the first model of what love is, you learn from observing your parents.

    23. TD

      Yeah. Uh-oh. Yeah, but you're right.

    24. SB

      Mm-hmm. You know? And then you go, "Okay, this is, this is love. Okay. So this man, this woman, how they interact." And then you grow up and you go ... That ne- never leaves your brain, and you think, "Is that what I want?"

    25. TD

      Right. That's right. That's right. That's right. Yeah. It is, it is not ...But you're right, and a lot of it is an excuse when, when I go, "Oh, it's all the rela- it's all the career," that's me being kind of a selfish person that, you, I needed to be selfish to figure out a way to, like, get to where I wanted to go. But, you know, I could have made more time, but I didn't, right? So it's like, you know, you battle a lot in life with, like, the things you want, the things you think you want. You know, it's kinda, you want the thing, you want the nice stuff, you want the nice cars, you want the nice things. But then you realize that the things you really like are the things that you feel drawn to. And you feel drawn to obviously making people laugh, but you also feel drawn to being, you know, in a, uh, like, a situation where you're being appreciated, loved, and, you know,

  20. 1:01:501:05:00

    What Do You Love About Yourself?

    1. TD

      taken care of.

    2. SB

      What do you love about yourself?

    3. TD

      My ability to do it and keep doing it. And, like, I don't, I'm not an excuse person. I don't, uh, I, take, you know, I, I take rejection and I, I kinda move on pretty quickly. I've done that since I'm a kid. Um, I have a lot of the qualities that a lot of the YouTube, uh, guys try to... Not, not the go to the gym every day and do this and do that, obviously, but, like, I don't let someone tell me something's not gonna happen. I'll just keep going until I figure out a way to make it happen on my terms. And I like that about myself at all. Uh, um, you know, I like that about myself a lot. I think that that's a good quality to have growing up the way I grew up. There's a version of me that's just a druggie, that's just on the street, that's dead, that is blaming everyone else for every other thing, that's talking about how, you know, whatever. So many people had it so much harder than me. Right? I had a mom that was sick and, you know, a dad that was maybe not as involved as maybe he could have been, but they're both really good people, both very supportive of me. The drugs were something that I did. They, you know what I mean? Like, so many people grow up in genuinely abusive environments, and they succeed wildly. So, I'm inspired by people like that. So I'm not trying to say like it's woe is me or anything, but, like, I did come from a, uh, an environment, and I do have that thing in me, we all do, where I could just offload everything and say, "Hey, I didn't get what I wanted. It wasn't a perfect scenario. I'm gonna use drugs for the rest of my life. I'm gonna mismanage my money. I'm gonna go broke. I'm gonna, you know, blame everybody else." I could have been that guy. I was that guy for many years, and I know who that guy is. I'm happy I was able to get rid of that. That doesn't mean the guy that I am now is a perfect person. Not at all. There's a whole host of other problems you have once you get rid of that guy, but I'm glad I got rid of that guy.

    4. SB

      And what are you working on now over there?

    5. TD

      I mean, everything. Eating better, sleeping better, uh, spending more time with people, going on dates and listening to actually what people say, you know, even if they're terribly uninteresting, as most of them are, right?

    6. SB

      (laughs)

    7. TD

      But you have to, you know, bless them. You have to... God bless them. They're children of God. You have to just kinda listen and, "You did? You majored marketing?"

    8. SB

      (laughs)

    9. TD

      So, you know, you, but, but all that stuff. Um, obviously I'm, I'm, I'm kidding. But, like, all of the stuff that human beings have to do, their mental, physical health, uh, you know, the way they balance their lives, it's, it's all... Once you sober up, it's not like, "Wow, the journey's done." It's like, "Wow, the journey can actually begin, and I can learn how to negotiate all this stuff as a human being." And you fail all the time, across the board. But what you don't do is you don't start using drugs, you don't start drinking, you don't start becoming a pathological liar. You don't start doing the things that you used to do when you were out there, you know, being the worst version of yourself.

  21. 1:05:001:07:27

    Mental Health Coping Mechanisms

    1. TD

    2. SB

      Coping mechanisms.

    3. TD

      Yeah.

    4. SB

      Mental health coping mechanisms. Uh, what's your, what's, how is your mental health, and, um, what are your new sort of mechanisms for managing mental health?

    5. TD

      Well, I, it's just, I think it's good I'm a comedian, so it can't be great. If it was great, I pro- I wouldn't have became a comedian probably. Um, I think talking to people, you know, taking long walks, again, helping people, enlarging your life, your spiritual life, trying to be a better person, um, is, is what everyone should do all the time. I think that's what I try to do. I try not to get too caught up in, you know, the insanity of the world, of spending too much time online, looking at the internet too much, you know, not being around real people, being in your head, obsessing about things you can't control, all of that. If you can, if you can find ways to not watch the murders on TikTok and go somewhere else and just sit on a beach or take a walk or do something, it's much better for your mental health than just watching this parade of insanity. You know, uh, it is fun to do. I do it sometimes. I have to do it as part of my show. But I think if you can get away from it... I, as I get older, I spend less time online. I grew up without it, and then it became your life. And now, if you spend less time on it, I actually think you look at it as, "Oh, this is something I do for my career," but then you actually have a real life. You can read a book and go somewhere. Like, that, to me, has more value now than just scrolling and the endless... That, that, to me, is a recipe for unhappiness. We know it too. All these young kids, we know how bad it is. We know how bad the effects of a lot of this stuff are, and we all lie about it. And all these tech companies are like, "There is no correlation between the mass suicide and my new app which tells them how to do it." Like, there's no, you know, there's no... You know, they have a new app, Suicider. They're like, "That has nothing to do with that." Um, you know, it's like, you know, uh, just filters which you can kill yourself. They go, "That has nothing to do with what's happening."

    6. SB

      (laughs)

    7. TD

      It's for entertainment, and the kids know it. So we know how bad this stuff is. We know how toxic it is. Um, we're seeing it with young people now the way we've never seen it before. And, uh, you know, so I think that's another thing. Your mental health can be really dramatically improved if you have a human, human interaction.

  22. 1:07:271:08:35

    Elon Musk Buying Twitter

    1. TD

    2. SB

      Elon obviously bought Twitter, and that seems to have kind of balanced the scales in terms of giving-

    3. TD

      Yeah.

    4. SB

      ... one could call it free speech-

    5. TD

      Yeah.

    6. SB

      ... but another outlet for people to just speak in a more uncensored, freer way-

    7. TD

      Sure.

    8. SB

      ... where they're-

    9. TD

      Yeah.

    10. SB

      Are you, are you happy that he, he bought-

    11. TD

      I think it was good, yeah. I mean, listen, Twitter had become a really unfortunate example of censorship in American society. Twitter itself, you know, as a thing is not a holistic thing. It never was. It was always this kind of battleground where people would just be crazy and, you know, fight with each other and this, that, and the other thing. I don't know that it is, you know, people say it's the town square. It might be. I don't know if it is. Uh, I think it's good that he bought it. I think it's good that people can say what they wanna say. Again, I, I just, I think that at the end of the day, it's like whatever Twitter is for people, if they really enjoy it or they like it, use it. You know, there are times when I enjoy it and I use it, and there's times when I just don't care as much, and I'd rather put those thoughts on my show and develop them more. I think that's, you know, where I'm at.

  23. 1:08:351:09:46

    Social Media Criticism

    1. TD

    2. SB

      Do you ever get, um, bothered by feedback you get?

    3. TD

      Sure, everyone does. Everyone does. But I don't get a lot of... I've tried to limit feedback because feedback can work in two ways. You can also start doing something you think people will like, and then end up destroying the beauty of what you do or, or what you enjoy. So I think when people go, "Well, why don't you do more of this? Well, I don't like this. This sucks. Do more of that," you shouldn't be in that headspace. You should go out and do what you do, and then the responses to it are all valid because the people that are having them, this is their reaction. But you don't have to consume their reactions as a way to program your mind about the things you create. I think you can let them have their reactions. And, you know, you can tell, you know, you can look and, and, you know, does what you're doing feel good? Does it make you laugh? Is it funny? Do people you trust and like enjoy it? And, you know, you know, in, in comedy there are metrics, right? Uh, there's all kinds of things, the internet, there's all kinds of metrics. Are people liking it? Did they buy tickets? Did they, are they enjoying it? People communicate in

  24. 1:09:461:15:03

    Touring The World

    1. TD

      all kinds of ways.

    2. SB

      So your tour.

    3. TD

      Yes.

    4. SB

      It comes to the UK. Very, very excited. I'm gonna do my very, very best to make sure I'm, I'm at least one of the shows.

    5. TD

      I would love for you to go, go to the one in Finland where 19 people have bought ticket. No, I'm kidding.

    6. SB

      (laughs)

    7. TD

      Um, that's, uh, I love the Finnish. A woman sent me a message. She goes, "It's not London, and it's not the Hamptons." But she goes, "It's what we have, and I'll show it to you." And I was like, "Well, I like that." I like someone who's very grounded like that, who really knows what it is.

    8. SB

      But the Royal Albert Hall, it's an iconic-

    9. TD

      That's the iconic venue, and I'm, I'm really happy to do it. And I'm so mad you're in Australia. We would have, you know...

    10. SB

      I, I'm pretty sure I'm in Australia on that day, aren't I? 'Cause I, when I saw you post on Twitter that you were coming to London, I sent it to my team within about a millisecond and said-

    11. TD

      Yeah.

    12. SB

      ... "Oh my God, let's all get tickets." And then someone rebuttaled and said you were in Australia at that time. But you're doing... You're in Manchester and Liverpool as well.

    13. TD

      Manchester.

    14. SB

      But the 7th of April, the Royal Albert Hall.

    15. TD

      Yeah.

    16. SB

      What, what can one expect from that show?

    17. TD

      I think if you are into darker comedy, if you like, you know, kind of, it's, it's, a lot of it's somewhat, you know, topical to a degree and look back at the year that we've kinda had, and you know, I talk about stories that have interested me in funny ways. You know, obviously, and there are, there are cultural trends in America, and probably a lot of them in Britain that, you know, we talk about all these things. A lot of the things that we've covered today, whether it's social media and its effect on children and mental health, all of these things are themes in The Hour of Comedy, right? And like people getting canceled for certain things, and homelessness I talk about because that's an epidemic in American cities, like drugs, everything. So a lot of what we've discussed today, it's, it's funnier there.

    18. SB

      (laughs) And you, um-

    19. TD

      Hopefully.

    20. SB

      You... I think I heard you say you were thinking about potentially moving to London at one point.

    21. TD

      I wanna... I'd love to own something in London. I like One Hyde Park, but it's very expensive. And the reason that I like it is because it's the most expensive residential real estate building in the world. No one really lives there, but you see these young Saudi kids drive their Bugattis and stuff, and every now and then, one or two lights is on. And it, to me, it symbolizes the utter coldness and emptiness of having things. And I think there's a beauty to that. There's something very interesting about it. You know, that whole city of London really interests me, and I don't mean the city of London. I mean that city of London, that city within a city, which most people don't know about, but there's a great article in Vanity Fair, read it or don't. The point is that whole area of Knightsbridge is very interesting to me, and One Hyde Park is interesting because the, the banality and the hollowness of extreme wealth really shocks. But we, we tend to... And listen, we know the rich are doing crazy things, right? The mega-rich, they create the yachts to this to that, the Epstein stuff, a lot of it not good, regrettable. We understand it. There's also an element I think people don't understand, and that's the banality, how boring, how passionless a lot of people are at that level of... And that's always made me, uh-

    22. SB

      You would like to join the Knightsbridge crowd?

    23. TD

      I, I... Well, I c- observe. You know, they'll never let me in. That's the other thing I love about... I'm addicted to rejection, right? Since I'm six, I've been auditioning and have, "No, no." So they'll never let me in. But it's just fun to kind of look at. And you don't even wanna be in per se 'cause it's not fun. That's the thing. It's not really that fun.... but it is funny to me when I look at, like, you know, the secrecy and how, you know, some of it really y- is really bad. And people doing crazy things, and they're overthrowing governments, and then, that's probably 10% of them, and then 90% of them, it's just they're fighting extreme suffocating boredom.

    24. SB

      And the north of England's very different, as you observed.

    25. TD

      Very spirited, lively, fun, interesting. I love it there.

    26. SB

      They like alcohol a little bit more.

    27. TD

      They love it.

    28. SB

      They have fun.

    29. TD

      They have a lot of fun, yeah.

    30. SB

      I guess they probably heckle you more.

  25. 1:15:031:17:40

    What Happens in Hollywood?

    1. TD

    2. SB

      M- yeah, I mean, California's a good example of a city in disarray. I couldn't quite believe it, 'cause the, um, the image we all have of California as Brits is this beautiful, clean-

    3. TD

      No, no.

    4. SB

      ... uh-

    5. TD

      Lie, lies. Hollywood lies.

    6. SB

      Well, th- that's what we've seen on our TVs.

    7. TD

      There are some, there are some beautiful parts of this state that are incredibly stunning, and you are, but it, the people are hollow. They're empty. They don't exist. All the people you meet in LA are figments of your imagination. They're fractals. They're not real. You didn't meet them. Uh, they are, uh, uh, an entity of which they are, they go between worlds, but they're not physically in reality the way that you are or I am. So keep that in mind as you're navigating this city, that the people, many of them that you're seeing, it's just kind of, you know, some of them are attractive and whatever, but they actually don't meaningfully exist in any way that you would understand.

    8. SB

      There's quite actually a thi- as you say that, there's a thin line between the two polar sides of LA, the extreme, like, wealth, and then the extreme poverty. There's, like, a thin line psychologically between...

    9. TD

      Most of LA is people waiting for instructions. That's what it is. Now, because everybody here is on the chopping block, from the CEO of Paramount to a busboy who's trying to get a showcase, uh, to get, uh, a spot at the Hollywood Improv or, uh, uh, maybe he wants to be an actor or whatever. Everybody in this town is replaceable. Everybody feels that. Everybody... So everybody's waiting for instructions. Uh, nobody wants to act. Everybody's waiting for somebody else to let them know it's okay because that is how the town works. And people tend to wait for consensus to build before they do something. You know, again, they don't believe anything. The town is not a town of people who believe things. They're, they sit in their house. They're sitting, you know, you, you look at these houses in Beverly Hills or wherever you are in Malibu, they're just sitting like this. They're just sitting like this, they're very still. And they don't, you know... And then they go out, their trainer works them out, they go back and they sit, and they stare. And they're waiting for instruction, they're waiting for the phone to call, they're waiting for an email. They're waiting to be told what to believe and who to believe in, and what reality is the reality of today. Are fat women in? Great. Get 'em on. Get a bunch of women in this on oxygen machines. What are we in today? Are we doing something else? Tomorrow, are we back to hot people? Get them. They're waiting for instructions. They have no beliefs. They are empty. They're hollow. They are vessels. Um, but it is pretty, and the tacos are good.

  26. 1:17:401:20:51

    Rising to the Top: The American Dream

    1. TD

Episode duration: 1:43:11

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