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 OBrien and is enjoying gratifying successworking
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, shes going to weigh more than the planet Earth.
And thats a problem, Conroy
According to his bit on Conan, Conroys
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 Conana
huge milestone, he sayscame after only three
years of professional performances. And in addition to the
momentum Conroy feels as a popular stand-up on the rise,
his actors baritone is tinged with the excited pride
of a young artist at the threshold of realizing his own voicesensibility,
imagination and perspective coming together in a clear vision.
According to Conroy, stand-up comedy isnt
what it was in its heyday, the late 80s and early 90san
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 Im 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.
Its a gradual process, and I dont know that Ive
fully figured it out yet, but I feel like Im going
in a specific direction, and I know what that direction is.
Conroys 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 Hes 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 Crossthe 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, Im going
to give you a job. I dont know what youre 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 masters degree
in science educationsomething 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 cant 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) didnt interest
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 thats 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? Thats
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 Brigadea sketch group that had its own show
on Comedy Central for three seasonshe 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,
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 Hes
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
Its just so much more interesting
than constantly trying to be funny, trying to be witty, he
says. Its 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 theyd
go to the theater, and if anyone showed up, theyd play
it by ear.
The theater was packed, Conroy
says. And we did a show. It wasnt the best show
weve ever done, obviously, but thats the only
time Ive 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 theres a place for people
who create joy.
Maria Healey is a free-lance writer from Northampton,
Photography by Robert Bennett 98