Joe List on How Tom Dustin: Portrait of a Comedian Is a Love Letter — and Maybe an Intervention

Joe List and Tom Dustin both started out as Boston-area comedians more than 20 years ago. They quickly became friends, drinking buddies and roommates, with a shared dream of moving to New York City to pursue comedy greatness.

List followed through on the dream. He got sober, scored a slew of TV appearances and standup specials, and started a thriving podcast, Tuesdays With Stories, with his friend and fellow comedian Mark Normand. He's also just directed his first film — a documentary — about his old friend.

Tom Dustin: Portrait of a Comedian tracks Dustin's decision to keep drinking and to relocate to Key West, Florida. He runs a comedy club where he does what he loves and regularly kills with audiences. But he's not well known outside of Key West, sometimes struggles financially, and wonders if quitting booze would be good for his mental health.

The film starts off by making clear that Dustin is very, very funny. He kills onstage, and feels loose and vulnerable and spontaneous. Offstage he's even more likable — fun, open, philosophical. As you watch, you find yourself wondering: Could Tom Dustin be a star?

The documentary makes you root hard for Dustin, and feel happy for his many sources of happiness. But it also makes you wonder if he could be happier.

"I did have this fantasy of ending the movie with a little title that would say, 'At the time of release, Tom's been sober for, you know, 248 days,' or something like that," says List. "I still hope that he does get sober, obviously."

As he made the film, he hoped that watching it might make Dustin decide to quit drinking. But mostly, List says, "I just wanted it be sort of a love letter to him, which to me, is what an intervention should be."

We talked with Joe List for the MovieMaker podcast about Tom Dustin, YouTube vs. theaters, and how you can be an offensive comedian and good liberal at the same time. You can listen wherever you get your podcasts, or — why not? — right here:

Joe List on the Martin Scorsese Film That Inspired Tom Dustin: Portrait of a Comedian

The documentary was shot over three-and-a-half-days in Key West, a freespirited town that feels like a Jimmy Buffett song. One mystery of the film is whether a guy who passed by on a bike actually is Jimmy Buffett.

But for all the sun-kissed tropical fantasies in Buffett's signature song, "Margaritaville," the chorus is about wasting away.

"If I was gonna relapse, I would go directly to Key West and meet up with Tom," says List, who, seconds later, promises that he won't do that.

Dustin is beloved by fellow comedians, in part for being so honest about exploring darkness. One section of the film deals with his rough childhood, which included his father's bouts with mental illness. At one point, his father was beaten with a tire iron in a violent misunderstanding.

There's sometimes a sense that sensitive subjects should be sidestepped, to protect the victims. But the victims don't always agree. Sometimes, they want to laugh.

When List showed the film to comedians, they laughed at the tire-iron story. No one in Dustin's family did — except his dad.

"His dad just thought that was really funny thing to re-live," says List.

List opened for Louis CK at the latter's peak, before his career was stunted by revelations of sexual misconduct you've probably heard about. List has stuck by his friend, and starred in his 2022 film The Fourth of July.

But when it came time to direct his own film, List turned to one of his favorite filmmakers, Martin Scorsese, for inspiration. Specifically Scorsese's American Boy, about his friend Steven Prince, who played the small part ofthe gun salesman Easy Andy in Taxi Driver. The director's approach was just to roll the cameras as friends and family told their stories.

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List took the same approach, and thinks Dustin's openness — especially when drinking — made the film more honest. Alcohol, List notes, "sort of accelerates emotion." But Dustin has some of his best moments while sober.

Dustin seems very moved in the film that someone cares enough to tell his story.

"He says at one point, he's like, crying, and he's like, 'It's the booze, you know?' And I don't know," says List. "If he wasn't drinking, he may not have been as open and as raw."

Tom Dustin Reacts to Joe List's Film About Him

Though List made clear that he was the focus of the film, sometimes Dustin couldn't believe it.

"We actually cut a lot of the times that he couldn't wrap his head around it. And I think he was just so touched by the fact that somebody was going to make a movie about him, and so that gave us a lot of emotion and feeling too," adds List.

"You're talking to him as a friend, but also, as a filmmaker, you're like, 'This is awesome. We're getting great stuff.'"

Dustin's emotionality and charm are among the reasons List thinks he would thrive in sobriety: 12-step programs, he notes, are built around storytelling and sharing.

"I think that he would really, really do great in sobriety, because he's such a social guy," says List.

One connection that improved because of the film is the one between Dustin and List. After years living far apart — List still lives in New York — they're talking more than ever, thanks to the film.

"So it kind of got us back together. It worked out," List says.

Tom Dustin: Portrait of a Comedian is now in theaters.

Main image: Tom Dustin, left, and Joe List. Photo by Matthew Salacuse