We Might Be Drunk – Ep 248: Harland Williams
Date: September 8, 2025
Hosts: Mark Normand & Sam Morril
Guest: Harland Williams (with drop-ins by Shane Gillis, Artie Lange, and more)
Episode Overview
This episode welcomes comedian, actor, and director Harland Williams for a riotous, freewheeling discussion about comedy, filmmaking, New York adventures, industry changes, and the unpredictable magic of hanging out with stand-up world notables. The episode is equal parts absurd riffing, candid inside-baseball on movie-making, and reverent comedy shop-talk. Surprise pop-ins by Artie Lange and others add to the loose, hangout feel.
Key Discussion Points & Insights
1. Drinks and Morning Mayhem ([00:06]–[03:20])
- Opening bit: The crew riffs on Harland’s quirky drink combo: Mountain Dew, Ready Whip, and Swiss Miss hot chocolate (“I like to keep winter alive” – Harland, [00:13]) with plenty of breakfast judging and jokes about odd beverage choices.
- Mountain Dew nostalgia: Harland references old Mountain Dew ads: “Remember the old ad, Yahoo. Mountain Dew?” ([01:07]) sparking stories about youthful theft and antics.
2. Comedy Culture, Live Stand-Up, and NYC Stories ([03:20]–[10:59])
- Comedy in NYC vs. LA: Harland shares love for New York, notes rarity of his visits, and Mark offers to help book him a spot at the Comedy Cellar ([09:17]).
- Joking about everything: Signature wild tangents ensue — from WNBA games and dildos smuggled on court ([03:24]) to placenta smoothies and umbilical cord drinks ([11:32]).
3. Comedy Trauma & Taboo Topics ([12:53]–[14:07])
- Peanut butter aversion: Harland, in his signature deadpan, riffs darkly on why he dislikes peanut butter: “When I was 4, my priest molested me while I was eating a peanut butter sandwich.” ([12:56]). The group riffs further, balancing dark with absurd.
4. Kill Tony, Roast Comedy & Panel Warfare ([15:06]–[19:53])
- Harland’s Kill Tony experience:
- Mark calls Harland “one of the best panel guys.”
- Harland describes going on Kill Tony with no prior knowledge: “I didn’t know who anybody was… This guy, David Lucas, comes out and starts coming at me. And I’m like, well, this ain’t gonna happen.” ([17:19])
- The viral video where Harland “destroys someone’s career” is discussed, but Harland clarifies there’s no real animosity.
- Advice for panel shows: “Just have fun. That’s my motto.” – Harland ([15:31])
5. Making Movies: Indie Hustle & DIY Filmmaking ([20:23]–[38:41])
- Harland’s new film, Wingman:
- Nearly ready for release via direct-to-fans digital platform, inspired by Shia LaBeouf’s model ([20:50]).
- Movie shot in just 15 days for just over $2 million (with Canadian government grants and private investors) ([38:18]).
- Candid advice: “If you try and compact everything at the beginning, it’s less painful surgery at the end.” ([26:27])
- Mark & Sam’s movie project:
- Loosely inspired by their real struggle as liquor salesmen in a sober, vaping new generation ([35:32]).
- Seeking $3–5M in funding, aiming to shoot in NY or wherever makes sense.
- Harland stresses need for flexibility: “A big part of it is learning to be able to adjust and adjust on the fly… learning to adapt quickly and move along. It helps” ([37:53]).
6. Industry Changes: Comedy Distribution & The Death of Late Night ([71:04]–[84:00])
- Direct-to-fan era:
- “If you had just, you know, 10,000 fans download your movie for 10 bucks a pop, that’s like 250 grand or whatever right there… I think fans… would support those movies 100% because they don’t get them in the theaters…” – Harland ([71:04])
- The group agrees a seismic shift is happening, with podcasts and independent releases replacing legacy gatekeepers.
- Late-night irrelevance:
- “Now you go to a comedy club, and you never hear it. None of the comics are worried about getting on late night. They're both more excited to get on a podcast.” – Harland ([77:53])
- Shift from crafting ‘Fallon sets’ to focusing on social media and stand-up specials.
- Conan as lifeboat: Mark notes Conan was scoffed at for jumping to podcasts, but will outlast other late-night hosts ([83:21]).
7. Comedic Memories, Influences, and Losses ([41:08]–[61:01])
- Rodney Dangerfield stories:
- Harland reflects on their friendship: “Held his hand… Then later that night, he passed away.” ([50:00])
- Rodney’s undying creativity and warmth for young comics.
- Shane shares Rodney’s post-surgery joke, delivered while groggy: “Rodney, did you cough anything up? And he goes, yeah, $500 last week to a whore.” ([48:22])
- Unheralded geniuses:
- Tribute to Montreal’s Sean Keane – “He was a prolific writer… but he was also paranoid about people stealing his stuff and that held him back.” ([53:00])
- Discuss loss of icons: Norm Macdonald, Patrice O’Neal, Greg Giraldo, Bernie Mac, Mitch Hedberg.
8. Drop-ins and Classic Bits ([27:00]–[34:00])
- Artie Lange & inside-comedy banter:
- Pop-ins bring a chaotic lunch-table energy; jokes about comedy careers, gigs, and the blend of gritty reality with absurdity.
- Memorable mention: “You're the dildo on the WNBA court. Yeah. Coming right in.” – Mark ([27:28])
- Reminiscence about legendary comic bits and infamous viral moments.
- Plugging upcoming shows and international dates.
Notable Quotes & Memorable Moments
- On Late Night TV:
- “Now you go to a comedy club, and you never hear it. None of the comics are worried about getting on late night. They're both more excited to get on a podcast.”
— Harland Williams, [77:53]
- “Now you go to a comedy club, and you never hear it. None of the comics are worried about getting on late night. They're both more excited to get on a podcast.”
- On Comedy DIY:
- “I think fans of ours… are excited to see us do our own projects. They don’t get them in the theaters… So I think… Wingman can sort of be a platform that works and fans come out and order it.”
— Harland Williams, [71:33]
- “I think fans of ours… are excited to see us do our own projects. They don’t get them in the theaters… So I think… Wingman can sort of be a platform that works and fans come out and order it.”
- On the gatekeepers falling:
- “Now I feel like the walls are starting to collapse… we can hopefully get stuff directly to consumers and not have to be at the mercy of these big entities.”
— Harland Williams, [77:02]
- “Now I feel like the walls are starting to collapse… we can hopefully get stuff directly to consumers and not have to be at the mercy of these big entities.”
- On panel show combat:
- “I went out and this guy, David Lucas comes out… and starts coming at me. And I’m like, well, this ain’t gonna happen. You come at me, I’m gonna come back at you.” — Harland, [17:19]
- Rodney’s post-surgery zinger:
- “Rodney, did you cough anything up? And he goes, yeah, $500 last week to a whore.” — Shane, impersonating Rodney ([48:22])
- Pay for roles you never did:
- “I got a check for a movie I wasn’t even in… I was supposed to do the voice of a snake, and they ended up giving it to George Carlin. And I still get royalties…” — Harland, [67:35]
- Absurd callbacks:
- “You can use the umbilical cord as a straw to drink the placenta.” — Harland, [11:51]
- “That could just close them. It smells like Cracker Barrel Meatloaf.” — Harland, riffing on Mark’s shorts, [02:34]
Important Segments & Timestamps
| Timestamp | Segment | |-----------|-----------------------------------------------------------| | 00:06 | Opening riff: drinks, breakfast, Mountain Dew nostalgia | | 09:17 | Harland’s thoughts on NYC, booking comedy spots | | 15:06 | Kill Tony, Roast Comedy, panel advice | | 17:19 | Harland vs. David Lucas on Kill Tony | | 20:23 | Harland’s movie ‘Wingman’: financing and indie production | | 35:32 | Mark & Sam pitch their liquor-salesmen movie | | 41:08 | Rodney Dangerfield stories & legacy | | 50:00 | Harland at Rodney’s deathbed, creative persistence | | 53:00 | Sean Keane tribute, dangers of business ignorance | | 71:04 | Direct-to-fan movie sales; demise of gatekeepers | | 77:53 | Death of late night TV, rise of podcasts for comics | | 83:34 | Conan, podcasting, legacy TV metaphor | | 84:35 | Who shouldn't podcast? Obama, celebrity podcasts flop | | Ending | Tour dates & closing banter |
Final Thoughts & Episode Tone
The episode is warm, loose, irreverent, and candidly insightful about the practical and creative realities of being a modern comedian and indie filmmaker. Absurd gags (placenta smoothies, peanut butter trauma), sharp jabs at the fading old-guard industry, and genuine affection for comedy’s lost legends all come together.
Harland Williams shines as a deadpan raconteur and indie film evangelist, dropping comedy pro-tips as often as he sabotages any moment with absurdity. Mark, Sam, and the drop-in guests bounce between bro hang, thoughtful reflection, and relentless riffing in classic "We Might Be Drunk" style.
Listeners will come away with:
- Real talk on the new era of comedy production/distribution
- Insider war stories from famous comedy venues and shows
- Unfiltered laughs and plenty of bits you’ll be quoting (“use the umbilical cord as a straw…”)
- An appreciation for the irrepressible energy and unpredictability of the stand-up world
Recommended action:
Look for Harland’s film “Wingman” on its forthcoming digital release. Catch all the comedians live on their just-announced tours—if you want more unfiltered stories and big laughs, their live shows are the place to be.