Joe List Made Documentary About Alcoholic Comedian Friend

"I'm always frustrated because I think a lot of people perceive comics as the ones everyone knows who live in New York and L.A.," says Joe List, a stand-up comic who may not be household name material like Jerry Seinfeld or Kevin Hart, but still manages to pay New York rent without selling a kidney. "There are thousands of comedians that no one has ever heard of who are making some kind of a living at this."

In February 2023, List—who's been nursing filmmaking dreams since his acne-riddled teenage years—decided to put his money where his mouth is. We're talking more than $25,000 of his hard-earned comedy cash, which in comedian economics is roughly equivalent to a small country's GDP. His mission? Shine a spotlight on Tom Dustin, a comic who's practically unknown on a national level but worshipped like a deity in Boston and Key West, Florida, where he currently resides and owns the aptly named Key West Comedy Club.

The result is the charmingly scrappy independent documentary "Tom Dustin: Portrait of a Comedian," now available on Punchup Live for a measly $6—less than what you'd spend on a decent sandwich, and infinitely more entertaining. The 96-minute film has been making rounds at festivals and even scored theatrical screenings, proving that sometimes the best stories come from people you've never heard of.

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What "Portrait of a Comedian" lacks in Hollywood polish—this is List's directorial debut and occasionally feels like an ambitious home movie shot by your most talented friend—it makes up for in raw authenticity. List, who also grew up in the Boston area, and Dustin are the kind of ride-or-die friends who'll tell each other exactly how much they suck, then buy the next round anyway. Their conversations are sometimes painfully direct, like watching your therapist get therapy.

Between clips of Dustin's razor-sharp standup sets, we see the man himself—rarely without a drink or cigarette, as if they're essential comedy accessories—talking candidly about his and his father's bipolar depression, his ongoing tango with alcohol, and the regrets he's collected like vintage vinyl records. Yet somehow, Dustin comes across as a guy who's genuinely comfortable in his own skin, not the tragic figure you might expect from that description.

The stories alone are worth the price of admission. Take, for instance, the legendary tale of how Dustin and List got robbed blind by a trio of prostitutes during a drunken New Orleans adventure—a story that's equal parts cautionary tale and comedy gold. It's the kind of yarn that only gets funnier (and more horrifying) with each retelling.

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List, who's been sober since 2012 and hosts the wildly popular "Tuesdays with Stories" podcast with Mark Normand, Zoomed with us from a Denver park during a break from his sold-out shows to discuss his documentary debut.

**Was making a documentary always sort of on your bucket list?**

I have so many things I want to do. I want to make narrative features. I want to make documentaries. I want to make short films. I want to do standup. I want to play professional baseball. I want to go to the dentist. I want to be in a band. It's one of many things I always wanted to do. I always try to take the path of least resistance. A documentary is definitely easier than writing a script, getting actors, and rehearsing. Of all the things I wanted to do, it seemed like the most doable—like comedy, but with more crying.

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**Was it fairly inexpensive to make?**

In terms of movies, it's a very cheap, low-budget affair, but I paid 100% of it out of my own pocket, so it was certainly more than my financial advisors would have recommended. Think somewhere between $25,000 and $30,000. It was a three-person crew—my friends Patrick Holbert and Matt Salacuse handled most of the camera work while I shot some B-roll footage that probably looks like it was filmed during an earthquake.

We had two cameras, no sound guy, and Patrick did all the editing. Then we hired someone to color-correct, which took forever. Plus I had to fly the crew down, put them up, and then—here's the kicker—we paid $7,000 just for one John Prine song. That was literally one-third of our entire budget. Music licensing is like buying designer drugs for your movie.

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**Why did you want to make Tom Dustin the subject of your documentary?**

There were a few reasons. Tom is such an interesting guy—we've been close friends for 25 years, and he's got a million great stories. The very earliest idea was just to film Tom telling these incredible tales because he's hilarious and one of those classic comedy characters. I think I say it in the film: he's pure comedian—a comedian to the core, like if you cut him open, joke setup would spill out instead of blood.

Then what ended up happening was he gave us so much about his mental health and emotions and feelings toward me that it became way more than I expected and better than I expected. Plus, there's the whole thing about him running his comedy club, and yeah, he's an alcoholic—though I'm happy to report he hasn't had a drink in over two months now.

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**I was reading some reviews, and one writer guessed that you might have done this because you didn't think Tom would be around much longer.**

I hope he lives forever, obviously, but I really wanted to capture this guy while I could. He's such a legend in Boston comedy circles. Every comedian who's met him—and that's a lot of comedians—when they heard I was making a movie about Tom, immediately said, "That's going to be incredible." The challenge is convincing people who don't know him yet.

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**It's clear from the documentary that you guys have a deep friendship.**

Yeah, it's really beautiful, though I'm such a mental case myself that I have a hard time processing feelings without immediately making jokes about them. But Tom got really emotional and open about his feelings for me—and crucially, he did it behind my back, which somehow makes it more meaningful. It's easier to trust compliments when someone doesn't know you're listening.

**Tom talks about being bipolar, and his father's mental illness. A lot of creative people seem to struggle with depression mixed with anxiety.**

Absolutely. I don't know why this is, but it's like a package deal with creativity. I struggle with horrible anxiety, depression, and OCD—the full neurotic starter pack. Just last night I was walking around this gorgeous park in Denver after an amazing sold-out show, and I'm sitting there thinking, "Oh my god, I've got to completely change my life. I don't know what, but something's fundamentally wrong."

Tom's father was bipolar, and I think Tom is too. There were times when we lived together and he just wouldn't leave the house for days and days. Wouldn't shower. Depression is such a hard thing to understand, but I think part of it has to do with an overactive mind—certainly that's the case with anxiety. And if your mind is overactive, it gives you lots of time and space to think of creative things.

Nowadays, I don't know anyone, artist or not, who isn't at least a little depressed. Social media hasn't helped—you get these amazing compliments and think, "Wow, I'm the man," but then you also get people telling you you're a piece of garbage. And your brain always believes the negative ones more because they "see the real you." There's never been a more difficult time to be a sane artist.

**I love how at the beginning he's in a suit and then you see him walking around Key West in Winnie-the-Pooh pajamas.**

We only shot like three and a half days in Key West, and one of those days happened to be during an onesie pub crawl. Key West has these events where everyone puts on onesies and stumbles around to different bars. So for one-third of the movie, Tom's dressed as Winnie-the-Pooh, which is either the most professional thing ever or the least professional—I honestly can't tell.

**Tom talks about a high school breakup that made him want to be a comedian. Was there a pivotal moment for you?**

I don't think there was one specific moment. Like I said, there were so many things I wanted to do, but I was obsessed with standup as a kid. I was born in 1982, right in the middle of the comedy boom. When I was 9, 10, 11, 12, comedy was everywhere—VH1, MTV, HBO, A&E. My family would rent Gallagher videos, or Elayne Boosler, or Louie Anderson, George Carlin, or Cosby—back when you could say his name without everyone getting uncomfortable.

We'd have dinner, then say, "Okay, time to pop in the comedy tape." I was the youngest, so while my siblings were out doing teenage things, it would be me and all the adults. It was one of the few times I really saw the adults in my family genuinely enjoying themselves, laughing until they cried. I thought, "Maybe if I do that, my parents will like me too."

**You're also from Boston?**

Yeah, I grew up in Whitman, Massachusetts, about 35 minutes south of Boston—far enough away to avoid most of the accent, close enough to inherit all the neuroses.

**I've heard that supporting up-and-coming comics is important to you.**

Absolutely. I've been incredibly lucky in my career. Boston has all these old legends—guys like Don Gavin, Tony Vee, Mike Donovan, and Kevin Knox, who's passed—who were so good to us young comics. I got to open for all these guys at the Comedy Connection. Nick Di Paolo took me on the road, Gary Gulman took me out, Colin Quinn became a mentor, and later Louis C.K.—back when that was still a good thing to say.

I've always collected these father-like figures who helped me enormously. So I try to be as good as I can to younger comics because I remember being in that desperate, "please just let me get stage time" position for so long.

**You thank Joe Rogan in the credits. Do you consider yourself part of the "manosphere"?**

I don't know about all that. I was just in Austin last week at the Mothership—incredible club, didn't see Joe, but the place is amazing. I've done Rogan a few times, but I'm definitely not a comic who blew up from Rogan. If you look up my appearances, it's mostly people going, "This is the worst guest ever. This guy sucks. He's boring." His fans think I'm some cuck liberal idiot.

I really like Joe as a person. Politically, I was disappointed he endorsed Trump, but I think he's genuinely a good guy. He's incredibly nice to comics and built something special for both young and established comedians. Even though I disagree with much of what Joe does, I think it comes from the heart. He genuinely believes it. Critics say a lot about Joe, and I get it, but much of it feels misguided.

**What's next for you?**

Right now, we're in preproduction on a documentary about SkankFest—which is an unfortunate name that makes it sound way more scandalous than it is. It's just a big comedy festival that Luis Gomez started. I also just released a new comedy special called "Small Ball" that hit theaters nationwide, and I'm constantly touring. I'm in Denver right now at Comedy Works all weekend with a completely new hour of material.

The thing is, I'm on the road constantly—not as much since I had a kid, but still a lot. I do five shows a weekend, and by the fifth show I'm like, "I literally cannot say this same shit again." It's ADD mixed with wanting to create something different. Once you're performing for people who are actually coming to see you—which is nice—it makes me want to come up with new material. It's easier because you don't have to win them over; they already like you, so whatever you're saying, they're on board.

**Do you like being on the road?**

I love it, but it's gotten complicated. My son is almost two, and he's really attached to me. He gets genuinely bummed when I leave, which breaks my heart. I'm mindful that there's limited time at each age, so leaving is much harder than it used to be.

But at the same time, I can get more done because when I'm home, he's hanging on me constantly. We don't have a nanny, so it's full-on dad mode. Sitting in Denver right now, I love exploring new neighborhoods. I like the isolation of being one-on-one with my opener, bouncing jokes back and forth. I love the shows, I love traveling, and frankly, New York is a city you're happy to leave for a couple days.

**Your wife, Sarah Tollemache, is also a stand-up comedian. How do you manage dual careers with a toddler?**

We basically take turns doing spots. She'll do a show one night while I stay with the baby, then we flip it the next night. If we both have spots, we have a couple of babysitters—both our nieces live here, plus a friend across the street. When I work cities where we have family, we'll bring the whole gang so someone can watch him while she opens for me.

A couple times she's gone on the road while I've stayed home playing Mr. Mom. It's just a matter of taking turns and doing our best. So far it's working out beautifully.

**You were wearing a Springsteen shirt last time I saw you. Big music fan?**

Huge music guy. Springsteen and Pearl Jam basically raised me—I've seen Pearl Jam live 53 times now, which is either dedication or a cry for help. I'm from a very small, blue-collar town, so Springsteen spoke to me as a kid and still does as an adult. I always say Bruce Springsteen is the most important person I've never met.

I'm also a massive Clash fan, love The Pogues. Being born in 1982, I'm all about that '90s stuff—Pearl Jam, Soundgarden. Huge Tom Petty guy. The Stones are my third favorite band. I'm a Dylan obsessive, and obviously love singer-songwriter stuff like John Prine—hence that expensive song in the documentary.

I'm also a closet punk—love the Ramones and Buzzcocks. Recently I've gotten into jazz and blues. Basically, anything that doesn't require a computer to make, I'm probably into it.