What Happened After the Joke: A Stand-Up’s Harrowing Tale

If there’s one thing comics want besides laughs, it’s to avoid being hack, which means, essentially, cliché. But defining hack can be tricky. It varies from room to room and changes with the times, a moving target that requires vigilance and alertness to track. No one dodges it with as much persistence as Gary Gulman.

His stand-up has long found creative ways to ridicule well-worn expressions (“I can’t even begin to tell you; I’ll begin to tell you,” went one digression), and he delights in playing devil’s advocate (see his remarkably persuasive case for Vanilla Ice). Another time, when he started a hypothetical about going to prison, he said, “If I didn’t have a boyfriend, I would get one soon,” pausing to let the countless cheap jokes about jailhouse sex set expectations, before heading in the other direction: “Because I’m a good listener.”

Gulman, 49, doesn’t just avoid hack comedy. He sees it as an opportunity, a tool to stand out. His riveting new special, “The Great Depresh,” which debuts Saturday on HBO, displays his signature contrarianism while also being a departure, since its darkly confessional style is firmly in keeping with what’s in vogue in the comedy special today.

His most characteristic move is a full-throated defense of millennials. In an era when comics incessantly bemoan woke culture on podcasts or in interviews or specials, Gulman is the rare middle-aged standup that celebrates sensitivity. He comes in praise of the snowflake. It’s almost startling to hear a club comic (Gulman is a regular at the Comedy Cellar in New York) express respect for participation trophies and tolerance for nonconforming gender roles and identities.

“I grew up in a time where the definition of manhood was so narrow,” he says. “You were either Clint Eastwood or you were Richard Simmons. There was nothing in between. There were no Paul Rudds. No kind-eyed Mark Ruffalos.”

Gulman has been a meticulous joke writer for years, a reliable killer on late-night shows, if not a star in the larger culture. In part, that’s because his finest jokes don’t hit you in the gut so much as tickle your brain. They have a literary quality, a rhythm and an ear for language that leads him to favor unexpected words (“cretin”) and phrases (“limit your quench”). As David Letterman used to do in his late-night monologues, Gulman savors a colloquial term, repeating it until the mundane starts to sound odd. “Millennials take so much flak, so much guff,” he says, enjoying articulation, spitting out sounds with gusto. “Flak as well as guff. I don’t know what irritates me more, the flak or the guff.”

He doesn’t overexplain punch lines, which can sometimes put him ahead of the audience. In “Depresh,” one joke about how drinking Sprite in the 1970s could raise questions about your masculinity assumes a bit of knowledge of “A Midsummer Night’s Dream.”

In his last special, “It’s About Time” in 2016, Gulman expanded his ambition, earning a big comic payoff by fitting jokes into longer set pieces including the digression-rich epic on state abbreviations that is probably his most famous joke and one of the finest bits of the decade. Patton Oswalt has said he would steal it if he could get away with it. As respected as it was among comedy fans — and Gulman has enough stature among comedians to give out daily advice on Twitter, which has become a window into the craft of jokes — this joke did not make him famous, or happy.

He sank into a paralyzing depression, the central subject of the new special, which blends stand-up with footage from his life, including scenes with his mother, wife and therapist. These elements are juggled confidently by the director Michael Bonfiglio, who opens with a vignette that evokes a 1970s sitcom. “Depresh” is produced by Judd Apatow, whose track record (“Knocked Up,” “Trainwreck,” “Girls”) reveals a knack for building mainstream vehicles to rocket comics up a level of stardom (Next up: Pete Davidson).

While Gulman’s previous output has been standard hours of loosely connected material, this special is slicker, more vulnerable and thematically integrated. It has the entertaining pace of a Hollywood movie about a comic, but one in which the story supports the stand-up as opposed to the other way around.

A tall, athletic guy with long hair, Gulman does not look like the stereotype of an insecure outsider, but he establishes himself quickly as a gentle giant. Once the applause quiets down, he says with a pointed excess of earnestness: “You came!” He later sums up his childhood economically: “Picture Charlie Brown, had Snoopy died.”

We see a clip of him bombing in a club after his last special, then hear him describe dropping out of comedy and moving home with his mother. He talks about crying jags and biting his lip until it bleeds. His story gets increasingly harrowing, as he checks into a psychiatric hospital, and sometimes the darkness pops up in the twist of a joke. “I really feel in some ways my aversion to essays has saved my life again and again,” he says, “because any time I contemplated suicide, I think: You’ve got to leave a note.”

A scene of him talking about his illness juxtaposed with his mother describing his childhood as happy-go-lucky is affecting in a way that telling jokes will never be. It’s a moving special, one that says explicitly what is only in the subtext of his previous work. (His last special’s opening, in which he talks about his laziness, now reads differently).

And yet, a comic digging into mental illness to both normalize it and find laughs has been done before by, among others, Maria Bamford and Chris Gethard. In fact, documentary about the relationship between comedy and depression, “Laughing Matters,” premieres on October 10.

“The Great Depresh” is not Gulman’s funniest special, though it has some great jokes, including an inspired bit about water fountains, but it’s the one that will probably appeal to the largest number of people. It has far too many fresh takes and idiosyncratic elements to be called hack. But it is a reminder that whatever you think about it, there is no denying that sometimes, the familiar works.

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