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