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The Comedian

Sean Conroy ’88 has one of the hottest stand-up acts in the country.

By Maria Healey

Sean Conroy '88When I catch up with Sean Conroy ’88, he has just spent three hours baby-sitting his niece. Conroy recently made a stand-up appearance on Late Night with Conan O’Brien and is enjoying gratifying success—working with an improvisational comedy troupe called The Swarm, performing for two years running to sold-out Friday night houses at the Upright Citizens Brigade in New York City. Nonetheless, Conroy, who, as the oldest of five brothers, has had plenty of baby-sitting experience, sounds hesitant and concerned.

“When my niece was born,” he says, “she weighed 8 pounds, 5 ounces. Nine months later, she weighs 24 pounds. If this keeps up, by the time she reaches retirement age, she’s going to weigh more than the planet Earth.”

“And that’s a problem,” Conroy says.

According to his bit on Conan, Conroy’s own weight is a matter of concern, living as he is on a diet of “Buffalo Wings, beer, and hope.” It seems to be serving him well, however. The appearance on Conan—“a huge milestone,” he says—came after only three years of professional performances. And in addition to the momentum Conroy feels as a popular stand-up on the rise, his actor’s baritone is tinged with the excited pride of a young artist at the threshold of realizing his own voice—sensibility, imagination and perspective coming together in a clear vision.

According to Conroy, stand-up comedy isn’t what it was in its heyday, the late ’80s and early ’90s—an original, in-the-moment art event between performer and audience. Once comedians started popping up on television, the culture of comedy clubs died out. Audiences stayed home, and comedians became “the minor league for Hollywood.”

For Conroy, though, stand-up “is an art form, something I’m really trying to learn and practice as a craft. Being a stand-up is all about connecting with the audience, trying to figure out who you are on stage. It’s a gradual process, and I don’t know that I’ve fully figured it out yet, but I feel like I’m going in a specific direction, and I know what that direction is.”

Conroy’s career began with a childhood love of acting. Growing up, he admired Steve Martin and “worshipped” Peter Sellers. An interest in performing led to involvement with the Alternative College Theatre (ACT) at Holy Cross, where he did two or three plays a year, learning how to project his voice and deliver a line. Preferring musicals and comedies to dramas, Conroy discovered that performing was “all about an opportunity to be funny. I always had this idea that I was hilarious. Nobody necessarily agreed with me. In fact, I played rugby for about five minutes when I was at Holy Cross, and the award the team gave me was ‘The Guy Who Thinks He’s Funnier Than Everybody Else.’”

In his third year, he began performing with The Crusadists, a sketch comedy group in the tradition of Saturday Night Live made up of drama students who “rigorously wrote these very elaborate scripts,” Conroy says, “satirizing various aspects of life at Holy Cross—the infirmary, the faculty, the students’ dating life.”

Ironically, though he was not “the most polite, helpful student,” the Jesuits’ passion for teaching rubbed off on Conroy nonetheless, and he went on to become an educator after college. Having moved to New York to pursue acting, Conroy worked as a full-time teacher from 1989-1995, teaching junior-high students for one year at 114th St. and Frederick Douglas Boulevard. and for five years on the Upper East Side. Before becoming the stuff of one-man shows, the experiences found their way into stories Conroy told “over and over again,” one of which describes an experience on his first job.

“The principal said, ‘I’m going to give you a job. I don’t know what you’re going to do yet, but you went to a Jesuit school, so you can teach anything.’ I ended up teaching math and science and social studies and English.”

Teaching full time and going to graduate school (Conroy dropped out 10 credits short of a master’s degree in science education—something “that delighted my parents even more” than his dream of succeeding in show business), he grew frustrated, doing only a couple of shows a month.

“You can’t get good at anything doing it that rarely,” he says.

In 1992, he founded his own comedy troupe, called “Out There,” so he could work more. From this, he got hired into Chicago City Limits, an off-Broadway touring company that has been running for 20 years. Still teaching at the time, Conroy flew all over the country on weekends to do shows but found that “my goals had shifted so much at that point, (doing company work) didn’t interest me anymore.”

What interested him was stand-up, writing and performing his own material.

“The stuff that works for me is more personal rather than just observational about people in general,” Conroy says. “Stuff that’s really happened to me, where I take the basis of a truth and say, ‘OK. Where does this go? How far can I push this and still have it be believable?’ That’s when I have the most fun, when something happens in real life, and I can transform it.”

After taking classes in improv with the Upright Citizens Brigade—a sketch group that had its own show on Comedy Central for three seasons—he struck out on his own with a one-man show called “Who Do You Think You Are?” The show got fine notices and in 2001, Conroy followed it up with a new piece that featured material from his teaching days, “a cohesive narrative (about) this 22-year-old white kid from Holy Cross in a totally black, urban school.”

The new show, “Taught,” received stellar reviews, prompting invitations to perform at several festivals, including the HBO U.S. Comedy Arts Festival, the biggest comedy festival in the country.

“Norman Lear came and saw the show,” Conroy says. “He came over and told me he enjoyed it. The King of American sitcom liked my show.”

No longer “The Guy Who Thinks He’s Funnier Than Everybody Else,” but now a guy “other people think is funnier than a lot of other people too,” Conroy currently teaches improv classes at Upright Citizens Brigade and performs every Wednesday, Friday and Saturday night at the UCB Theater, doing various shows. His favorite is the Friday night show with The Swarm, “this incredible group of talented people who all trust each other so much that we can do anything we want to whenever we want and know that ultimately it will work on stage.”

The Swarm specializes in “Long Form Improvisation,” where the troupe takes one suggestion from the audience and uses that as inspiration for a 45-minute sketch. Conroy thrives on the creativity inherent in such a spontaneous, organic process.

“It’s just so much more interesting than constantly trying to be funny, trying to be witty,” he says. “It’s more sophisticated, more truthful, more about real human experiences, as opposed to making a pun on orangutan.”

Speaking of real, human experiences, Conroy mentions the night The Swarm ended up doing a show on Sept. 13, two days after Sept. 11. After agonizing as to whether or not they should perform, the troupe members decided they’d go to the theater, and if anyone showed up, they’d play it by ear.

“The theater was packed,” Conroy says. “And we did a show. It wasn’t the best show we’ve ever done, obviously, but that’s the only time I’ve ever had a bunch of people come up to me after a show and say, ‘thank you.’ It was a strange experience, but it made me feel that there’s a place for people who create joy.”

Maria Healey is a free-lance writer from Northampton, Mass.

Photography by Robert Bennett ’98


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