CHAPTERS
- 0:00 – 1:30
Revisiting the Boston comedy boom (late ’70s–’80s) and why it felt unique
Joe welcomes Don Gavin and frames the conversation around the legendary Boston stand-up era. Don explains how the scene grew from small rooms into a full-blown comedy explosion, and why “Boston style” was more about intensity than a single approach.
- •Joe’s admiration for Don and the 1980s Boston comedy ecosystem
- •Don starts in 1979 and describes the scene’s rapid growth
- •No single ‘Boston style’—but a common aggressive energy
- •Different comic voices coexisted and pushed standards higher
- 1:30 – 2:30
The Ding Ho roots: hostile rooms, DIY beginnings, and early innovators
Don describes the Ding Ho as a rough saloon that resisted becoming a comedy venue. He recounts how early comics carved out space, built a community, and effectively created rules that later became part of the local culture.
- •The Ding Ho wasn’t a comedy club at first; patrons fought the change
- •Early names: Barry Crimmins, Lenny Clarke, Sweeney, DJ Haz, others
- •Learning stand-up in public with no roadmap
- •The scene’s early ‘trial by fire’ atmosphere
- 2:30 – 5:05
The ‘headliner hosts’ Boston format and running multiple rooms in one night
They break down the unusual Boston practice of having the headliner host, doing interstitial minutes between comics. Don explains the practical motivation—control of pacing and quality—then describes the chaos of running five shows across multiple rooms at Nick’s.
- •Headliner-as-host format and why it gave the host control
- •Cutting struggling comics short to protect the show’s momentum
- •Nick’s: shows upstairs/downstairs/disco—comics cycling between rooms
- •The logistical confusion and repetition by the fifth show (and drinks)
- 5:05 – 8:26
Party culture and the IRS crackdown: cash payments, audits, and fallout
Joe and Don shift to the darker side of the era: nonstop partying and getting paid in cash. Don details how the IRS caught him, what the audit process felt like, and how massive interest charges ballooned the debt.
- •Boston comics’ heavy partying and casual attitudes toward taxes
- •Getting caught via a Boston Globe calendar feature
- •Years of negotiations, lawyers, and repeated IRS contacts
- •Owing six figures largely due to interest and penalties
- •Widespread IRS trouble across the scene; a few ‘responsible’ exceptions
- 8:26 – 9:40
From teacher to full-time comic: burnout, a car crash, and choosing comedy
Don shares his early double life as a high school teacher by day and comic by night. A near-fatal fatigue-related crash forces him to choose, and he ultimately leaves teaching to pursue stand-up full time.
- •Teaching during the day while staying out until 3–4 a.m.
- •Quitting teaching around 1984 after years of overlap
- •Falling asleep at the wheel and crashing hard (windshield injury)
- •Realization: one job had to go—comedy wins
- 9:40 – 13:54
Breaking in before open mics: auditions, early pay, bombing, and a Lenny Clarke fight
They compare today’s open-mic pipeline with Don’s era, when you had to audition for club bookers. Don recounts earning $8, experiencing an early catastrophic bomb, and getting into a fistfight with Lenny Clarke that strangely became the basis for friendship.
- •In 1979 there weren’t open mics; comics were auditioned
- •Comedy Connection origins and the ‘comedy class’ pathway
- •First paycheck: $8; doing the same early 10 minutes repeatedly
- •Writing ‘15 minutes’ in a day leads to a brutal bomb
- •Fistfight with Lenny Clarke turns into lifelong friendship
- 13:54 – 17:14
Why Boston exploded: dense clubs, packed lines, and the scene’s later dilution
Joe and Don map the club density on Warrenton Street and beyond, recalling lines in winter and constant work. Don argues the decline came when non-comic owners chased profit, over-expanded venues, and diluted quality.
- •Multiple clubs within 100 yards; crowds lining up in snow
- •Comedy clubs were still a young national phenomenon
- •Satellite rooms and constant paid work across town
- •Decline factors: owners replacing comics, greed, ‘every corner a club’
- •Audience disappointment when quality dropped
- 17:14 – 19:50
‘Murderers’ row’ and the outsider gauntlet: setting up visiting headliners
Joe explains how Boston clubs would stack local killers before a national headliner, creating impossible comparisons. Don confirms it was often intentional, and they share stories about famous comics struggling with the Boston crowd’s pace and standards.
- •Local lineups designed to overwhelm visiting headliners
- •Story of Billy Crystal bombing after locals destroyed the room
- •Richard Lewis publicly complained about the Boston gauntlet
- •Boston audiences demanded rapid punchline density
- •Outsiders weren’t used to the aggressive pacing
- 19:50 – 31:46
Fast talk, Irish roots, and ‘savages’ on and off stage (plus brawls)
They dissect what made Boston comics feel physically and stylistically intimidating: speed, toughness, and a culture where fights weren’t unusual. Don ties his rapid delivery to big-family dynamics and describes how club brawls became part of the lore.
- •Don’s high words-per-minute delivery; ‘asides’ and tags
- •Irish Catholic cultural influence and big-family ‘talk fast or lose out’
- •Perception gap: comedians as insecure vs. Boston comics as tough
- •Brawls at clubs and the Ding Ho’s rowdy environment
- •Joe’s early impressions and Don’s feedback on Joe’s early ‘dirty’ act
- 31:46 – 36:08
Drugs, drinking, and the Ding Ho after-hours: cops, cards, and sunrise exits
Don details how substance use became normalized in the scene and how the Ding Ho served as a late-night hub. He describes staying until morning, partying with cops present, and the club’s abrupt end after the owner’s gambling loss.
- •Vices ‘blossomed’ after entering comedy; social proof drove use
- •Ding Ho as the epicenter: lines, joints, drinks, card games on stage
- •Cops drinking with comics—little fear of getting busted
- •Ding Ho closure: owner loses $240,000 gambling; doors padlocked
- •Legend status among later Boston comics who never experienced it
- 36:08 – 40:01
Touring realities and industry scams: Houston stories and Spotlight Agency theft
They broaden to other scenes like Houston and Chicago and how single clubs can define a city’s comedy health. Don tells a notorious story about Spotlight Agency/agent fraud, plus wild road anecdotes that capture the era’s rough edges.
- •Houston’s Laff Stop scene parallels Boston’s intensity
- •Don’s revenge story: water balloon leads to smashed car windows
- •Chicago’s scene decline tied to club closures and ownership issues
- •Spotlight Agency scam: broken promises, unpaid comics, major losses
- •Leno/Seinfeld and others reportedly hit hard by the scheme
- 40:01 – 41:58
The modern Comedy Store and comedy ‘tourism’: packed rooms without the coke
Joe contrasts the old days with today’s Comedy Store, now fueled by internet awareness and constant lineups. Don reacts to how global fans travel specifically to see the Store, and they discuss how the culture has shifted toward weed and away from fights.
- •Comedy Store now packed nightly; schedules drive visitor planning
- •International fans flying in specifically for comedy lineups
- •Three-room ‘madness’ reminiscent of Nick’s peak—minus cocaine
- •Cultural change: fewer fights, more marijuana, occasional mushrooms
- •Comedians running the asylum vs. purely business-minded ownership
- 41:58 – 49:02
Don’s album release: ‘Live with The Manhattan’ and finally going digital
Don explains he recorded an album in 2011 but never truly ‘released’ it beyond selling copies informally. With help from a comedy network, it’s now appearing on SiriusXM/Pandora and moving to major streaming platforms.
- •Album recorded in 2011; material kept evergreen by avoiding politics
- •Previously sold like a bootleg from his trunk after shows
- •Jimmy Serpico helps produce and distribute through proper channels
- •Availability: SiriusXM, Pandora, then broader streaming rollout
- •Joe’s advice: consistent content output to build audience
- 49:02 – 54:02
Writing process, recording sets, and building jokes: stage-first experimentation
They get tactical about joke writing: jotting premises, testing placement, and refining on stage. Joe explains why he sometimes opens with new material and how recording sets preserves spontaneous punchlines; Don weighs adopting newer habits.
- •Don writes premises with pen; fleshes out ideas on stage
- •Where to place new material (sandwich vs. opening)
- •Joe’s ‘open with new’ strategy and the risk/reward calculus
- •Importance of recording sets to capture improvised gold
- •Family-life workaround: Joe runs off to voice-note ideas instantly
- 54:02 – 1:06:07
Tech reluctance, social media catch-up, and the ‘godfather’ debate
Don jokes about being late to phones, texting, and Instagram, while Joe emphasizes modern promotion. They also touch on Boston comedy politics—particularly Dick Doherty’s ‘godfather’ claim and Don’s view of mentorship as the real credential.
- •Don’s first text to Joe; voice-to-text fails due to accent
- •Launching Instagram: ‘Don Gavin Comedy’ and early posting basics
- •Buying/claiming handles and the cost of name ownership online
- •Joe highlights podcast appearances as modern career leverage
- •Don challenges Dick Doherty’s ‘godfather’ label based on mentorship
- 1:06:07 – 1:14:21
Road audiences: best and worst regions, plus international quirks (Memphis, Connecticut, Australia)
They swap regional crowd experiences—Joe singles out Connecticut while Don recalls a brutal Memphis week. They also discuss how cultural gaps affect jokes overseas, like Halloween material failing in Australia when audiences didn’t share the reference.
- •Joe’s least favorite: Connecticut; favorites include Texas and England
- •Don’s worst week: Memphis—fast talk, ‘Yankee’ stigma, visible clock
- •Tactics when a room collapses: stalling, heckling tables, surviving sets
- •Australia’s evolving culture—Halloween once unfamiliar to many
- •Rowdy but engaged crowds in England and Australia
