Laughter Worth the Price

Image by Jenna Szabo.

Image by Jenna Szabo.

Even as a Hollywood headliner who hit the big screen this year, comedian Jay Montepare ’00 likes to brag about something he pulled off as a child.

“Sometimes I would get my big brother laughing so hard he would literally pee the bed,” said Montepare, who shared sleeping quarters with his sibling early on. “And that would make me happy – which was weird because then we would have to sleep in a pee bed. But it was worth it to me just to know that I could do that.”

The brothers’ late-night joke-fests led to an L.A. career for Montepare that’s getting hotter every day. Known for his spontaneity and for pulling
audience members into his acts, he said he’s happiest on the stage, which he’s shared with the likes of Drew Carey, Sarah Silverman, and Joe Rogan. But, Montepare said, making a living making folks laugh isn’t always what it’s cracked up to be.

“I got into comedy thinking I’d be around people all the time,” he said. “It can be lonely. You travel all over the country. You do your gig, get your check, go back to your hotel room, and watch Everybody Loves Raymond for the umpteenth time.”

“You get one pitter, and you’re like, ‘I killed! They loved it!’” – Jay Montepare

Montepare wasn’t worried about any of that when he was growing up in Williamstown, Mass., making his brother laugh and getting inspired by comedians like Richard Pryor, Bill Cosby, and Louie Anderson.

“I would watch stand-up comedy, and it was so special and so daunting. I felt like the people who did it were superhuman,” said Montepare, who by fourth grade was doing stand-up in the classroom.

He brought his humor to college, where he majored in English and played baseball. With Rob Wall ’00 and John Langan ’00, he won Mary Washington’s first lip-sync contest, singing The Devil Went Down to Georgia. But when Montepare took a stab at stand-up at the Underground, some in the crowd mistook his message and walked out.

“Even though that happened, I still knew how it felt to get some laughs,” he said. “That’s the thing about comedians, you get one pitter, and you’re like, ‘I killed! They loved it!’ ”

He bumped up his act and took it to Richmond; to Boston, where he hosted The Tribe Presents comedy show; and finally to L.A., where he lives with his wife, actress and writer Elizabeth Chomko.

Besides doing stand-up, comedian Jay Montepare writes and performs on Will Ferrell’s

Besides doing stand-up, comedian Jay Montepare writes and performs on Will Ferrell’s
Photo by Jeff Lorch.

A regular at Hollywood hotspots like the Improv and The Comedy Store, Montepare has performed in commercials, on TV, and in movies; at colleges, including his alma mater; and for the troops in Japan. He writes sketches for Will Ferrell’s, and has an hourlong CD called The Sound That Jokes Make and a part in the recent comedy feature film Walk of Shame, with Elizabeth Banks and Kevin Nealon.

“There is nothing I’d rather do in this world,” Montepare said of his work as a comedian. “It’s hard to explain. You’re onstage and you can feel the energy of the crowd filling you up with power. It’s a feeling I’ve only felt when I was doing stand-up.”