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On with Kara Swisher

Rosie O'Donnell gets brutally honest on Trump, facelifts, and leaving America

Rosie O'Donnell joins Kara for a candid conversation about Donald Trump, leaving America, GLPs, plastic surgery, and parenting an autistic child.

Rosie O'DonnellguestKara Swisherhost

Aug 3, 202654mWatch on YouTube ↗

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CHAPTERS

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Chapter summaries

Opening bit: serenading Trump and setting the tone
Rosie O’Donnell opens with a comedic ‘love song’ aimed at Donald Trump, with Kara Swisher playing along. The playful start establishes the episode’s mix of humor, personal storytelling, and political commentary.
- •Rosie jokes directly to “Donny,” assuming he’s watching
- •Kara leans into the bit and moves the conversation forward
- •The episode’s blend of comedy and politics is signaled immediately
Returning to New York: Broadway, nostalgia, and feeling “re-famous”
Kara welcomes Rosie back to the U.S. and asks what she missed most. Rosie describes diving into Broadway and classic New York spots, and reflects on how public reactions to her feel like a return to an earlier era of fame.
- •Rosie says Broadway is her first stop when she’s back in New York
- •She and Kara praise “Jellicle Ball,” including its cultural meaning and why it works
- •Rosie notes people shouting to her from cars again and says she feels “re-famous”
- •She links renewed attention to nostalgia and to people wanting voices that stand up to what’s happening in the country
Ireland unlocks the show’s grief story: seeing her mother’s face everywhere
Rosie explains that living in Ireland led her to write deeply about her mother’s death, because she kept seeing older Irish women who resembled her mother. Kara and Rosie discuss how early parental loss becomes a lifelong grief shaped by what’s missing.
- •Rosie says Ireland prompted her to imagine what life would have been like with her mother still alive
- •She describes structuring the show around the day her mother died and their final exchange
- •Rosie says the grief doesn’t end and recalls Nora Ephron asking if it was her defining emotional moment
- •Kara and Rosie discuss how people who haven’t lost a parent young can struggle to relate
Why she left America: Project 2025, fear, and finding peace in Ireland
Rosie describes reading Project 2025 as the trigger that made leaving feel necessary. She frames the move as seeking safety for her family and mental relief from what she calls “Trump noise,” and she describes Ireland as welcoming and less fame-obsessed.
- •Rosie says reading Project 2025 convinced her it was time to leave if Trump got in
- •She says she felt threatened as a gay woman and as the parent of an autistic child and a non-binary child
- •Rosie compares ongoing political stress to “noise in my head,” calling it “Trump noise”
- •She describes Ireland as not being a fame culture and recounts people saying “You’re welcome home”
Parenting Clay in Ireland: inclusive school, safety, and boundaries around storytelling
Rosie details how Ireland’s public school system has been beneficial for Clay, emphasizing inclusion and everyday independence. She also describes negotiating what’s fair to share about her child in an autobiographical show and how Clay reacts to hearing rehearsals.
- •Rosie says Ireland’s public school has been more inclusive and helpful for her child
- •She tells the ‘lollipop lady’ crossing-guard story and how it changed their routine
- •Rosie contrasts Ireland’s safety with fears she has in New York and LA
- •She recounts Clay objecting to being included in the show and Rosie explaining she writes from her life
- •Rosie describes Clay correcting her from another room during rehearsals and Rosie keeping material as written
Coming out pressures in Hollywood: what it cost to be ‘first’
Kara recalls a past argument with Rosie about coming out, and Rosie explains why she feared doing it earlier. Rosie describes how people around her worked to keep appearances, and how officially coming out after 9/11 changed her life and made it more fulfilling.
- •Kara describes an earlier off-the-record debate with Rosie about coming out
- •Rosie says she didn’t believe an out lesbian performer could still work in Hollywood at the time
- •She recounts public-relations maneuvering to avoid being seen as coupled at events
- •Rosie describes how others removed suggestive lines from an interview without her asking
- •She says coming out made her life more fulfilling and less chaotic, and jokes about going “all the way gay” afterward
Trump feud origins: calling him a grifter, living with harassment, and why she won’t stop
Kara transitions to politics and asks about the personal impact of Trump’s repeated attacks. Rosie explains the feud began when she criticized him publicly and says she’s never regretted speaking out, framing it as a responsibility tied to what America allowed her to become.
- •Kara notes Trump attacked Rosie again and asks how it affects her daily life
- •Rosie says she told the truth about Trump on TV and describes him as not self-made and as a grifter and ‘logo slapper’
- •She says she’s seen who he was since she was a kid and believes speaking out triggered his obsession
- •Rosie says she feels responsible to speak up because the country gave her opportunities
- •She contrasts in-person experiences (mostly thanks) with online harassment, which she manages with blocking and filters
Billionaires and broken values: excess, victimhood, and the collapse of balance
Kara asks what’s happened to the current rich, and Rosie argues that people who only measure life in money lose their purpose. They discuss gross excess, corporate ownership, and how Ireland represents a different relationship to work, holidays, and “enough.”
- •Rosie says people who measure only in money have “lost the reason for living”
- •She contrasts having enough with continued excess and criticizes Jeff Bezos’ behavior toward employees and the symbolism of a lavish wedding
- •Kara and Rosie discuss wealthy people framing themselves as victims
- •Rosie says Ireland has a clearer concept of balance and “enough,” centered on work and long holidays
- •Rosie criticizes corporate ownership and warns that without a functioning fourth estate democracy is endangered
Trump, media, and ‘welcome back’: polls, persuasion, and forgiving the conned
Kara and Rosie discuss whether people are finally waking up to Trump and how to respond to former supporters. Rosie argues for welcoming back people who were conned, while also sharing a personal story about forgiving—then cutting off—someone who returned to Trump.
- •Rosie says people are waking up and describes Trump as treating politics like a reality show
- •She blames Mark Burnett for normalizing the idea that repeated TV lies become truth, and mentions Roy Cohen as well
- •Kara and Rosie argue for welcoming back some former Trump voters, despite pushback
- •Rosie recounts writing to Michael Cohen, visiting him in prison, then blocking him after he reconciled with Trump
- •Rosie says she replies “Thank you and welcome back” to people who express regret for voting for Trump multiple times
Democrats and late-night comedy: Megan Rapinoe’s question and Kimmel hosting plans
A recorded question from Megan Rapinoe prompts Rosie to describe how she’ll approach Trump on Jimmy Kimmel Live: comedic but truthful. Rosie shares frustration about being told she can’t do a political parody song, then previews her approach and offers blunt advice for Democrats.
- •Megan Rapinoe asks what Democrats can learn and how Rosie will handle Trump on Kimmel
- •Rosie says she’ll follow Jimmy Kimmel’s model: comedic, honest, and bold
- •Rosie sings part of a parody she wanted to do on the show and says she was told permission couldn’t be obtained because it’s political content
- •Rosie says Democrats should stand up to Trump strongly and match his force while staying intellectually superior
- •She argues Trump can’t be ignored because he’s constantly doing harmful things and enriching himself openly
Aging in public: GLP-1s, weight loss honesty, and a subtle facelift
Kara shifts to aging and asks why Rosie chose to be open about GLP-1s and cosmetic work. Rosie argues that public figures shouldn’t lie about dramatic changes, explains her gradual weight loss on a low dose, and describes choosing a doctor who would do only what she asked.
- •Kara notes Rosie looks different and asks about stigma around GLP-1s and a facelift
- •Rosie criticizes celebrities who deny using GLP-1s and later admit it
- •Rosie describes losing about 60 pounds over three years and dealing with extra facial skin
- •She explains she wanted subtle work and chose a doctor who agreed to do only what she wanted
- •Rosie says she told people it’s expensive and shares the doctor’s name while contrasting more extreme options
Feminism, body autonomy, and how GLP-1s changed ‘food noise’
Rosie recounts Clay’s strong objections to plastic surgery as a feminist issue, and how Rosie ultimately decided feminism means making her own choices. Rosie and Kara also discuss how GLP-1s reduced compulsive food-related thoughts, with Rosie describing how the medication changed her relationship to sugar.
- •Rosie recounts Clay calling plastic surgery a rejection of what Rosie represents and saying it might change how Clay sees her
- •Rosie says she ultimately chose the procedure for her own wellbeing and frames feminism as autonomy
- •Kara and Rosie compare it to doing things for themselves, like tattoos
- •Rosie describes intense ‘food noise,’ including searching for hidden candy, and says the drug changed her life
- •Rosie hopes prices drop so more people can access medications like Mounjaro
What comes next: returning when Trump is ‘done,’ the future of the show, and priorities
Rosie says she’ll consider moving back to the U.S. when Trump is no longer in power, largely because she misses her other children and wants Clay closer to siblings. She explains the one-woman show as a proof of concept, discusses Broadway possibilities and ticket pricing, and reflects on parenting in her 60s and staying centered for her family and mental health.
- •Rosie says she’ll move back ‘when he’s done,’ citing missing her other children and wanting sibling bonds stronger for Clay
- •She describes loving her home in Dublin and wanting to keep it while returning to the U.S.
- •Rosie explains the show’s New York run as a limited test and says a Broadway future depends on producing decisions and economics
- •She discusses the difficulty of touring with Clay and mentions autistic burnout from travel and lack of routine
- •Rosie reflects on being a more patient, more connected parent in her 60s and says her next act should prioritize family time; she rejects running for office due to mental health demands

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