Gary Gulman Can Make Absolutely Anything Funny

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One day in November of 2019, the comedian Gary Gulman was scrolling on his phone when a Tweet caught his attention. Jason Zinoman, the comedy critic for the New York Times, had posed a relatively innocuous question to his followers: “What stand-up have you liked that is about class (however you want to define it)?”

The prompt intrigued Gulman. He realized couldn’t think of a comedian who’d built a whole act around socio-economic status. George Carlin had touched on the topic, certainly, with riffs about how the ruling class operates to keep themselves on top. And plenty of comedians had made fun of rich people for being out of touch or joked about being poor themselves. “But I hadn’t seen anybody who made the entire hour about class,” says Gulman. “And I thought, ‘Oh, that’s it! That’s a great area.’ And then I just started.”

Gulman was fresh off one of the most triumphant moments of his career—and not far removed perhaps the lowest point of his life. Just a month earlier, his special The Great Depresh had premiered on HBO to glowing reviews. Gulman had built that act around his own battle with clinical depression, mining humor out of tough topics such as electro-shock therapy and art class in the psych ward. Interspersed throughout the live set were scenes filmed with his mom at his childhood home in Peabody, Mass., north of Boston, where Gulman had retreated in 2017 to regroup when his mental-health crisis was at its worst. His openness resonated with both critics and audiences. And that validation gave him the freedom to be more opinionated on stage, he says, after “doing mostly safe observational jokes for twenty-five years.”

The challenge of getting laughs out of a subject as potentially dry as income inequality energized Gulman. He immersed himself in reading books on poverty in America and the lifestyles of the ultra-rich. He returned to and reflected on the message at the center of Dickens’s A Christmas Carol, a story he’s been obsessed with since childhood and revisits every year. The material began to flow. Writing jokes about the class divide, says Gulman, “seemed to dovetail nicely with my unhealthy resentment towards billionaires and the one percent.”

The resulting act forms the heart of Gulman’s new comedy special, Born on 3rd Base, which premieres tonight (Thursday, Dec. 21) on MAX and was produced by, among others, Conan O’Brien. As in The Great Depresh, Gulman isn’t afraid to be vulnerable. He talks candidly about the fact that his parents struggled financially when he was a kid. “Welfare saved my family and I’m not ashamed to have been on it,” he tells the audience.

The special follows the publication in September of Gulman’s first book, a memoir called Misfit: Growing up Awkward in the ‘80s that chronicles Gulman’s life from the first day of kindergarten through high school. As in The Great Depresh, Gulman weaves in scenes from his mental health struggle, which led him to pack up his New York apartment and back to Peabody for a time to live in his mom’s house and sleep in his childhood bedroom. But the bulk of the book is a portrait of a sensitive, precocious boy growing up as the child of divorced parents, gravitating toward father figures and desperately seeking a close friend or two. Packed with vivid characters, Misfit is always witty and frequently hilarious, but also searingly poignant at times.

On the comedy tour he set up this fall to coincide with the release of Misfit, Gulman says he’s been signing books and posing for photos with fans for an hour or more after every show. “Everybody uses the word surreal too much,” says Gulman. “But it is kind of a dream come true. I've been on the other side of that situation a lot, where I go to meet an author, and I know how special that interaction is. So now to be on the side where I'm signing people's books, I'm very grateful.”

Between the publication of his memoir and the release of Born on 3^rd Base, Gulman, fifty-three, is experiencing a run of success and recognition that many of his peers would say is much overdue—some thirty years into his comedy career. If it’s a cliché to describe a stand-up as a comedian’s comedian, it’s one that is nonetheless apt in the case of Gulman. Over the years, he’s been booked on all the late-night shows, taped comedy specials, and built a loyal national following, all without ever quite breaking through. But while stardom has eluded him, he has earned a reputation among those in the know as perhaps America’s most literate stand-up working today.

“I think every comedian would agree that Gary is better than most everybody,” says Judd Apatow, who produced The Great Depresh and has long admired Gulman’s approach to comedy. “There are certain people you go, ‘Oh, they're on another level.’ Their artistry, their ambition, their willingness to try new things, how much they'll open up. No matter how many comedians there are, only a few are working at the highest level. And Gary is one of them.”

The humble Pop-Tart still looms large in Gulman’s mind. When his family was on welfare, Gulman tells the audience early in Born on 3^rdBase, he qualified for free lunch at school. That also meant free breakfast—if he could get there by 6:15 a.m. When Gulman arrived early enough, he’d be able to get a single Pop-Tart. Half of one package. As much as he coveted the breakfast treat at the time, he uses it in his act now as a symbol for the way that America demeans people struggling financially. “The Pop-Tart was just a complete F-you to the poor kids,” Gulman tells the audience, before detailing some of the many indignities.

“First of all, it’s not a real tart,” says Gulman. “The real tart has chunks of fruit: apples, pears, raspberries, blueberries.” He switches to a tone of disdain: “Whereas the Pop-Tart has a suggestion, of a rumor, of a whisper, of fruit-flavored, artificially colored schmutz. It's so fraudulent that the Pop-Tart calls itself a tart.”

Finally, he adopts a bit of mock outrage to offer his final word on the subject: “I used to think they called it a Pop-Tart because it popped out of a toaster,” he says to the audience. “No. ‘Pop’ is short for populist. It’s the poor man’s tart.”

Such word play is a hallmark of Gulman’s comedy. He thinks about language and vocabulary in a very precise, healthily obsessive way. Over the years, Gulman has honed a style of comedic storytelling that incorporates layers of detours and diversions, allowing him to weave in more and more jokes without ever losing the narrative. “He communicates differently than everybody else,” says Apatow. “And he's a real wordsmith. He cares very deeply about his comedy writing.”

The comedian Ryan Hamilton, who shared an apartment with Gulman and a couple of other roommates in New York in the early 2010s, echoes that sentiment. “Words are so special to Gary,” says Hamilton, “And he really has a gift for finding just the right word that can turn a joke.”

Hamilton says that having Gulman for a roommate was inspiring because Gulman was always writing and working on his craft. The apartment effectively didn’t have a living or dining room, because the living room had been turned over to one of their roommates for a bedroom. But Hamilton and Gulman would stand in the kitchen in the morning and talk comedy while eating bowls of cereal. “He was constantly threatening to start a newsletter that was just for our apartment, you know, with all the big news of the day about who left what in the fridge,” says Hamilton. “Seeing our apartment filtered through his comedic lens was really fun.”

Gulman has a rare talent for making an esoteric topic funny in a broadly accessible way. But sometimes that means sitting on an idea for years until he figures out how to make it work on stage. One of his best-known bits centers on a made-up Netflix documentary about the U.S. Postal Service’s effort to give every state its own two-capital-letter abbreviation. When Gulman’s fictional team of abbreviators gets stuck, they’re forced to bring in a contractor—as in a specialist at creating contractions. (“Can’t? Don’t tell me I can’t. Motherfucker, I invented can’t!”) Gulman says that he scribbled the original idea for the routine in a notebook in 1994 but it took him until around 2013 before he’d figured out how to successfully incorporate it into his act.

About five years ago, Gulman turned himself into something of a Twitter comedy guru thanks to an impulsive moment over breakfast. On the morning of Dec. 31, 2018, he was having coffee with his wife, Sadé, when he posed a question: “What do you think people would do if I offered a comedy tip every day next year?” She told him she thought they would love it. So he tweeted out that he was going to embark on the project, and then he followed through. For 366 consecutive days, Gulman scrambled to come up with and share fresh pieces of advice and, every once in a while, strong opinions about what not to do as a comedian.

The first tip he tweeted, on Jan. 1, 2019, remains his top piece of advice for comedians: “Record every set. The hard part: Listen to it and transcribe everything you want to say again. It’s sometimes depressing but it gets you to do the hardest part which is to sit down and write. Usually you’ll think of something to add or change. This works for me.”

Gulman is painstaking about analyzing his language choices. After transcribing his sets, he often circles a word here or there and tries to come up with a better option that's more fitting or more poetic, or more in rhythm. (Tip No. 6: “Words with the sound ‘buh,’ ‘puh,’ and ‘kuh,’ especially at the beginning/end are funnier. No one knows why. ‘Buick’ is funnier than ‘Nissan.’ I learned this early. I assumed everyone knew. They don’t.”) That fascination with language is bolstered by his appetite for reading. In casual conversation, Gulman often and easily cites the work of favorite writers like Kurt Vonnegut, John McPhee, Anne LaMott, and David Foster Wallace.

As hard as he works at it, Gulman is self-deprecating about his way with words. “I just I love to hear really smart people talk,” says Gulman. “And if you spend enough time writing, you can sound like a smart person.”

The first thing you notice when you meet Gulman in person is his height. A former high school basketball player—and, briefly, a Division I football player—he’s six-foot six inches tall and an athletic two hundred and twenty pounds. When we met for coffee at a café near Union Square in Manhattan one day in September, he was wearing a Knicks hat, a Bruce Springsteen Darkness at the Edge of Town t-shirt, and Boston Celtics star Jayson Tatum’s Nike basketball shoes.

On stage, his stature gives Gulman with a naturally commanding presence. But the contrast of his imposing physique and his inherent sensitivity and anxiety also combine for comedic effect. Gulman has a powerful sense of right and wrong—strong moral convictions about proper behavior in both the biggest and most quotidian of ways. “I’m always boycotting things,” he says in Born on 3^rd Base. He became vegetarian after watching the documentary Food, Inc. several years ago, and then went vegan as a New Year’s resolution in 2018. While we were talking in the coffee shop, Gulman became momentarily distracted by another customer who was conducting a sales call on his smartphone. “Can you hear me?!” the guy said way too loudly, as if in a commercial spoof. “I can hear ya,” said Gulman in a forceful, chiding tone.

Gulman grew up as the youngest of three boys. His parents divorced when he was 18 months old and he saw his father for visits every Sunday. Gary describes his dad, Phil Gulman, as a loving and supportive parent but one who didn’t always grasp his youngest child’s personality. Phil wanted to instill in Gary a pugilistic type of toughness that didn’t come naturally to him. Tall for his age, Gulman was also precocious (a word he uses about himself a lot, both in jest and not) and started reading at age four. Looking back at the anxiety he felt as child and the constant haze over his experiences, Gulman recognizes the early signs of clinical depression that would follow him into adulthood.

One of the central narratives in Misfit is the trauma that Gulman endured after his father persuaded his elementary school, over the objection of the principal and the counselor, to hold Gulman back for a second time through first grade so that he’d have another year to mature. It had nothing to do with academics; he was one of the best readers in his class. When he asked his father what to do if other kids teased him for being held back, his dad told Gulman he should “knock ‘em out.”

Money was tight. His mother lamented their financial situation all the time. Her favorite joke, says Gulman, was a line she must have borrowed from a comedian: “Next time I get married, I'm marrying for love—the love of money.” His father, too, worried out loud about money on his Sunday visits. His family was never hungry or homeless, but Gulman remembers his mother crying on the phone with the IRS at the idea that they might lose the house if she couldn’t pay her taxes. "I grew up in an oft-ignored sector of Jewish people called poor," he says in Born on 3rd Base.

The summer before his senior year of high school, a pair of enterprising assistant coaches sized up Gulman’s athletic frame and convinced him to try football for the first time. They put him on an intense workout plan. By August, he was a ripped two hundred and forty pounds. He made the varsity, earned playing time, and ended up making enough good plays for a highlight reel that got the attention of Boston College. Suddenly the sensitive teen who still loved Mister Rogers and secretly nurtured dreams of making people laugh on TV someday was signed up to play tight end at a big-time college football program.

It didn’t last long. As soon as he started practicing with the team, he knew he wasn’t cut out for the violence of the sport at the college level. His mental health deteriorated quickly. “I felt overwhelmed immediately,” says Gulman. “I was just so lonely and sad.” He made it through the fall season and the spring scrimmage, then went to a team counselor to tell him he couldn’t go on.

Gulman figured he’d have to drop out of school. But the counselor and the team trainer persuaded the school to honor his scholarship. Gulman graduated from BC in 1993 with a double major in finance and accounting and got hired by Coopers & Lybrand as an accountant. “I really was always so insecure financially that I wanted to figure out a way so I could prevent that in my adulthood,” he says, “not knowing that I was fearing insecurity in general, not financial insecurity.”

His career as an accountant lasted longer than his tenure as a college football player, but not by that much. Gulman performed his first stand-up set on October 11, 1993. A couple of years, he quit his accounting job to free up more time for comedy. He worked day jobs as a barista at Starbucks and as a substitute teacher at his alma mater, Peabody High School.

Then he got his first big break—or it appeared that way at first. He performed a tight, five-minute set at the Just for Laughs comedy festival in Montreal in July of 1999 and landed a $250,000 development deal with Fox. He was going to be a sitcom star! Gulman moved to Los Angeles and the network paired him with a writer. “We sat around, we wrote a pilot, and then they said, ‘No thanks.’” The next summer, he did another five minutes at a showcase in L.A. and got a similar deal with CBS. Again, it was turned down. And then the next year, he snagged a similar deal with Showtime. Same result. “I was making a really good living selling ideas based on my stand-up for sitcom pilots that never got shot,” he says. “It was so frustrating.”

Another breakthrough came in 2003 when Gulman finished third on Last Comic Standing, the reality TV competition show for comedians. The burst of fame enabled him to be a headliner for sold out shows around the country—for about six months. Then his fame faded and his ability to fill rooms fizzled.

He kept working and touring. And by 2015 he had put together what he knew was his strongest set of material yet. It included the Abbreviating the States bit and a twenty-minute routine about a showdown he’d had with a woman in Trader Joe’s, over her breaking the unwritten rules of the checkout line, that was a tour de force of Gulman’s comic digressions into everything from The Chronicles of Narnia to The Golden Girls. He taped a special called “It’s About Time” with full confidence that it would finally deliver him a bigger fan base. Instead, the producers had a hard time selling it and it wound up on Netflix at a discount rate months later.

While he was regrouping in his childhood home in the summer of 2017, Gulman started performing at a small club in Harvard Square called the Comedy Studio. It was above a Chinese food restaurant and the crowd, says Gulman, was a lot of students drinking scorpion bowls. But the owner was supportive and encouraged Gulman to keep coming back night after night even when he was struggling. His hands were shaky from anxiety, and he frequently couldn’t summon the willpower to shower or shave. “The only reason I even talked about depression on stage was because it was so clear that there was something off,” says Gulman. “I didn’t look well. I had to address why I felt so bad. And I felt very safe addressing it there.”

Pretty soon he had ten minutes of material on depression. Then twenty. His manager connected Gulman with the director Michael Bonfiglio, who agreed to work with Gulman and pushed him to keep developing the act and take more chances with the material. Soon he had enough for a special. Apatow came in as a producer, and not long after they were filming The Great Depresh for HBO. “They said yes in December. We shot it in June. And then it came out in October. There was never a hitch at any step along the way,” says Gulman. “I've never before in my life been a part of any TV show that wasn't a series of loops and discouragements and false starts.”

Gulman’s life has been on an upward trajectory ever since, both professionally and health-wise. His depression has now been in remission for six years. He moved back to New York in 2018 and he plays basketball virtually every morning to keep his body and mind sharp. “I’ve been living a charmed life,” he says. “It just took 46 or 47 years to get there.”

Meanwhile, not a day goes by where somebody doesn't send him a message or come to a show and say how important The Great Depresh was to them. And after coming out on the other side of his depression battle, says Gulman, he feels a sense of obligation to keep connecting with others who are suffering. “The only thing that I that I struggle with, really, is am I doing enough to spread the word about about mental health,” says Gulman. “Because I've come to the conclusion that it was it was worth me experiencing this if I can help enough people and get the message of hope out to enough to enough people My heart breaks for people because when you're in it you really it's it's really hard to see any way out of it.”

Given the subject matter of his new special, and Gulman’s experience growing up with limited means, my assumption was that the title of Born on 3^rd Base was ironic. Gulman certainly didn't inherit wealth or grow up in a particularly privileged environment. So I figured the name of the special must be another dig at the ultra-wealthy. But Gulman didn’t intend it that way. Even if his family was on food stamps at times, he recognizes that he was afforded a lot of opportunities in life that others weren’t. “In reality, I feel like I was kind of born on third base,” he says. “Because I was born a white male in the 1970s and I went into two sports and was given a scholarship based on just my DNA and my physicality. I was very lucky in a lot of ways.”

He had originally tried explaining this in his act, but it never got a laugh. And it felt contrived, because he’d come up with the name of the tour before he wrote the joke. “That was the twist,” says Gulman. “But I was just never able to make it into something that was funny.” And in the end, funny always has to win.

Photography: Aaron Richter
Styling: Alfonso Fernandez Navas
Grooming: Devra Kinery
Hand model: Andrea Rios

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