Podcast Summary: We Might Be Drunk – Ep 258: Roy Wood Jr.
Hosts: Mark Normand & Sam Morril
Guest: Roy Wood Jr.
Release Date: November 10, 2025
Episode Overview
NYC comedians Mark Normand and Sam Morril welcome Roy Wood Jr. for a spirited, joke-packed episode covering the grind of standup, touring stories, comedy industry changes, race and media in comedy, and how comedians adapt and thrive in the digital age. Along the way, they swap sharp anecdotes from the road, dissect the mechanics and culture of roasts, reminisce about legendary comics, and dig into Roy’s new book and career journey. The episode is rich in insight, laughs, and practical wisdom for anyone curious about the modern comedy landscape.
Main Discussion Themes
1. Touring and Comedian Life on the Road
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Halifax & Ottawa Shows: Mark shares highlights from recent Canada gigs, describing Halifax as a "hidden gem" with a great crowd and recounting wild misadventures in Ottawa, including running late and high-energy sets.
“Halifax… It’s one of those towns, like, thanks for coming. Nobody comes here. Cute. Beach town, lobster, water.” — Mark (00:44)
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Absolute Comedy Club: Both praise Canada's Absolute Comedy as one of the best clubs for working material, making tapes, and playing for smart, hot crowds.
“They used to say, you go there to make a tape… go up there. Everything kills. Cambridge. Just go clean.” — Sam (05:20)
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Sandler Tour Life: Sam dishes on touring with Adam Sandler, playing mega-arenas and enjoying “summer camp” vibes, with daily basketball, steakhouse dinners, private jets, and run-ins with stars like Kevin Nealon and Fortune Feimster.
“You fly private every day… it's a massive version of how I try to tour...” — Sam (10:00)
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Green Room Misadventures: Sam confesses to a disastrous moment — using Sandler’s green room bathroom with untimely results.
“I went in the green room bathroom. It was not a good shit. It was a red meat and whiskey shit.” — Sam (07:29) “Rob Schneider was there, and he goes, you can't give him ammo. He's going to use this against you forever.” — Sam (08:19)
2. Comedy Roasts & Cross-Cultural Roast Culture
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Jamie Foxx vs. Doug Williams, and the Anatomy of Roasts: The gang analyzes the infamous moment Jamie Foxx roasted Doug Williams mid-set, discussing its backstory and why roasts are trickier in Black comedy contexts. Roy offers nuanced context, noting that Foxx's heckling was payback for Doug's off-camera bravado.
“Jamie just starts pretending to be his conscience… what every comedian has when you're bombing, you're thinking to yourself the whole time.” — Roy (21:00) “I just don't know if you could organize a situation for any black celebrity to just sit there while other black celebrities just belittle him.” — Roy (21:51)
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Comparing Roast Cultures: They explore why Black entertainers rarely do mainstream-style roasts, discussing trust, authenticity, and communal ties.
“The idea of get him back, and I roast out of love — it would have to legitimately be people out of love.” — Roy (22:11)
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Comedy Central Roasts: The group reminisces about the early days, behind-the-scenes stories, and limitations of industry roasts, including why some line-ups feel cold and impersonal (Chevy Chase, Bruce Willis, etc).
3. Industry Wars: TV Specials vs. YouTube & Self-Producing
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Changing Comedy Distribution: Roy details his journey through traditional TV specials (Comedy Central, Hulu, Paramount+) and doubts the value of waiting for industry validation.
“There's still some sort of prestige to… industry. Of course, when the truth is that the industry probably doesn't fucking matter that much.” — Roy (46:04) “Waiting on the coding, waiting on the tech to catch up. Yeah, it was fucking horrible.” — Roy (48:00)
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The YouTube Revolution: Mark and Sam describe their move to YouTube out of “desperation,” realizing later it was the smartest move as platforms like Comedy Central lost relevancy with locked, geo-fenced content.
“It was an act of desperation. It wasn't like business savvy on our part.” — Sam (56:40)
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Advice to Comedians: The importance of self-released content, sharing resources, and constant reinvention — with practical strategies for reaching wider and younger audiences.
“Find what you love. Find a place it can live and do it over and over again.” — Roy (69:32) “Any comic is better off just doing 15s every month… then chop them down to 90 seconds for social.” — Roy (50:10)
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Race & Comedy Networking: Mark asks why “black comics shoot fewer YouTube specials.” Roy attributes it to quest for industry legitimacy, lack of strategy-sharing, and cultural differences in networking.
4. Legacy, Evolution, and Comedy Preservation
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On Adaptation: Reflecting on George Wallace, John Witherspoon, Gaffigan, and Seinfeld, they discuss how comics survive generational shifts by staying nimble and relevant.
“You only do that if you can reinvent, invent constantly.” — Roy (66:07)
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Immortality of Comedy: They praise Comedians in Cars Getting Coffee and the Comedy Museum in Jamestown, NY for preserving legacies and intimate stories of legendary comics.
“Comedians in Cars is the closest thing to this in terms of immortalizing conversations with comedians.” — Roy (74:40)
5. Comedian Relationships, Burnout, and Support
- On Helping Others: Roy and the hosts talk freely about the challenges of mentoring, setting boundaries, and pouring energy into others’ careers.
“Do you ever hit a wall of not wanting to help people anymore for feeling like you haven't helped yourself enough?” — Roy (58:35)
- Partner/Personal Support: Roy shares lessons from Spanky Brown and others about needing support in relationships and the impact bad energy can have on creative work.
“If you're going to be with somebody, choosing somebody that actually complements what you do or is in support of it… you can't be no spoiler.” — Roy (93:25)
6. Audience Building, Demographics, and Longevity
- Turning Audience Over: They discuss how as comedians age, their fanbase skews older unless they actively seek to engage younger fans through new media.
- Importance of Platforms for Growth: The internet presents opportunities for new audience discovery every day, but only if comics share and publish their work widely.
Notable Quotes & Memorable Moments
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On the comedy touring life:
“Touring with Sandler is like summer camp. Steakhouse every night. By night three, I'm going to feel sick from all this red meat.”
— Sam Morril (06:32) -
On the infamous Jamie Foxx roast incident:
“Jamie just starts pretending to be his conscience, which is what every comedian has when you're bombing, you're thinking to yourself the whole time.”
— Roy Wood Jr. (21:02) -
On old-school vs. new-school distribution:
“Comedy Central – they really were living like it was 1992. Here's one airing of that thing you worked for years on.”
— Sam Morril (47:01) -
On self-producing:
“I should have took 30k and shot that bitch myself. If I'd have shot that bitch myself in 2016, what the fuck would that number be by now?”
— Roy Wood Jr. (56:29) -
On sharing knowledge:
“There’s no master class for how to do stand up shit. Share it. We'll share it ... I’ll talk. Any young comic who’s like, really, really wants it, I’ll fucking answer you.”
— Sam Morril & Roy Wood Jr. (57:44–57:56) -
On lasting relevance:
“You only do that if you can reinvent, invent constantly.”
— Roy Wood Jr. (66:07)
Key Timestamps
- 00:44 — Mark & Sam rave about Halifax and Ottawa as comedy towns
- 06:32 — Sam’s stories of touring with Sandler and private jet life
- 07:29–08:23 — Sam’s green room faux pas and ribbing from Sandler & Schneider
- 21:00–24:11 — Dissecting the Jamie Foxx/Doug Williams roast incident
- 31:54–34:02 — Industry “gotcha” takedowns, cancel culture, and bouncing back
- 46:04–50:14 — Roy compares Black and white comedians’ strategies & the YouTube pivot
- 56:17–57:56 — The "YouTube special" revolution explained
- 66:07–67:54 — How comics survive by evolving and finding new audiences
- 73:07–75:38 — The importance of the Comedy Museum and immortalizing comedy legends
- 84:53–85:53 — Mark’s “Cameo” birthday surprise from Mark McGrath (Sugar Ray)
- 86:26–88:35 — Roy discusses writing his first book, family dynamics, and emotional challenges
- 90:28–92:51 — Lessons in standing one’s ground and personal relationships from Spanky Brown
Episode Mood & Tone
Raucous, honest, and naturally conversational with tightly woven punchlines and open reflections. Jokes about the process and lifestyle mingle seamlessly with sharp, practical advice and behind-the-scenes stories. The camaraderie is tangible, and the episode captures the lived-in reality of comics who love their craft enough to constantly adapt, critique the status quo, and look out for each other.
Closing Notes & Plugs
Roy Wood Jr.:
- New book out now—stories about fatherhood and life lessons
- Fall tour: Book included with each ticket
- Catch Roy on CNN's panel show
Mark Normand & Sam Morril:
- Upcoming shows all over the US and Europe
- Check out their YouTube specials
- Bodega Cat Whiskey now available (ask your local bar/comedy club)
“Find what you love. Find a place it can live and do it over and over again.”
— Roy Wood Jr. (69:32)