Demetri Martin is trying out something new on his latest tour: live drawing

Boston Globe

25-06-2025

'It's a game to me, and what's cool is that when I add my words to my drawing, it becomes activated differently,' Martin says.
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On this tour, Martin also continues his quest for concision, with what may be his shortest joke yet: 'Fish fish,' a comment on the idea that aquatic creatures hunt and eat their seafaring brethren.
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(He confesses that his drive for efficient jokes — 'remove, remove' is his credo — is a challenge for filling an hour. 'It's not a great game, because I'm just making it harder on myself,' he says.)
It's all in keeping with the man who once joked, 'Sometimes I think I overthink things. But other times I ask myself, 'Do I?''
Growing up on the Jersey Shore, Martin, 52, felt out of place in the macho, sports-driven world. 'I was the weird one,' says Martin, whose cerebral but silly one-liners often call to mind the sensibility of his early influences Steven Wright and 'Far Side' cartoonist Gary Larson.
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'I liked drawing and I was on the math team. I liked poetry and guitar,' he says. 'No one was doing that in my family or showing me those things.'
The teenage Martin also found validation in puzzle books, which both suited and shaped his brain. 'I think somehow that became joke writing for me once I got into comedy,' he said in a recent video interview. 'When I watched comedy, I liked predicting punch lines — they were like puzzles for me.'
Martin's solving skills also propelled him to Yale University, where he wrote
Planning to become a lawyer, he earned a seat at Harvard Law but then switched to New York University for a full scholarship, only to drop out after two years to pursue stand-up.
His breakthrough came in 2003 when his one-man show, 'If I,' won an award at Edinburgh Fringe. It showed off his quirky intellectual humor, but it also included more personal musings. Doing a nightly show about himself was too much. 'I couldn't handle that,' he reflects. 'With my one-liners, even if there's a personal connection, the jokes mean I'm at least one step removed from them.' (This reserve is why he is 'one of six comedians in America without a podcast' as he explains on this tour.)
While he built his stand-up career, he wrote for '
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The show also taught him discipline and the need to find different twists and structures. 'It was like joke-writing boot camp,' he says. 'I learned to try to stay a step ahead of the audience.'
That often means staring at a joke or drawing, saying, 'What am I missing?'
'My wife always teases me, because I say that so much it's like a weird mantra — it's the existential thing, but also just asking: Why can't I figure this out? It must be right in front of me.'
Martin works constantly on new material, in part because he has learned that when he doesn't, rust accumulates and can be hard to shake, but also because his brain is always revving on high.
'I was at a dinner party once and said, 'I wouldn't say I'm tortured' and my wife started laughing. I meant I'm not depressed,' Martin recalls. 'But she said, 'Your brain is a non-stop barrage and you can't stop.''
But he argues that comedy has helped him embrace that. 'I direct the stream into something positive and productive by writing jokes — I get to have a job but also prevent my thoughts from turning back on me and analyzing this and that.'
When those deadpan jokes take a second or longer to land, it can be tough to tell if they worked. At a recent show in Brooklyn, he did a bit about realizing all phone numbers having a negative number in it. The crowd didn't respond much and Martin backed away. When I mentioned that it would be helped by an actual example, he said he usually does it that way: 'When I try to give people my number, I say it's 240, negative 3567 or whatever. But last night I got discouraged so I didn't do the tag. But I should.'
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After that show, I overheard a group of friends walking together and recounting his jokes, still processing some of them. 'It's comforting to hear that,' Martin says, explaining that he forgets that his jokes can take time to process and so he's sometimes thrown off when people don't laugh in the moment.
Martin still likes challenging himself. 'I'm still searching for different games I can play,' he says, like drawing live on stage for this tour. He sometimes accompanies his jokes with his guitar, finding witticisms that are enhanced by the combo, either because they fit the rhythm or are propelled more by the music and sometimes will try finding jokes that work while accompanied by minor chords.
His new tour begins with him offstage, doing a longer, more conceptual joke than most Martin material: He encourages the audience to prepare for comedy by closing their eyes and relaxing; he adopts the soothing tones of a meditation coach but undercuts every bit of instruction by working in an analogy to something connected to the chaos of modern life in America.
'That was a fun experiment,' he says. 'I really think comedy is an art. And the stage is such a great canvas. It's such an opportunity to have a direct conversation with the people who've come to see you.'
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DEMETRI MARTIN
At the Wilbur, June 28, 7 p.m. and 9:45 p.m. 246 Tremont St., Boston.