Kevin Flynn is home for the holidays and he is excited to bring his one-man comedy act to the Shoreline

MADISON—While Kevin Flynn’s career has taken him all over the world, he is happy to be back home helping to raise money for The Friends of Madison Youth, a nonprofit organization that offers theatrical performances, social events, workshops, camps and community activities to Shoreline youth at the Madison Arts Barn.

“Fear of Heights,” Flynn’s one-man show, is Saturday, Nov. 30, 8 p.m. at the Madison Arts Barn, 8 Campus Drive, Madison. No one under 21 years of age is permitted, as there is a cocktail hour, 7 – 8 p.m.

Tickets are $35 in advance and $45 at the door. To order tickets visit For additional information email or call 203-245-2689.

“We’re hoping it means bringing in some much needed funds,” says Madison Arts Barn Co-Director Tammy Boris, a friend of Flynn’s from Daniel Hand High School.

Ask Flynn if he is funny and he doesn’t hesitate with his answer.

“Yes, I am,” he says. “Bought a house and put my kid through school.”

The mission of the Madison Arts Barn is near and dear to Flynn.

“…when I heard about the Madison Arts Barn, they always kind of struggle for funding and I thought I could help them out for the kid’s programming,” says the 58 year-old.

Every year, Flynn invites all his comedy pals to the Nantucket Comedy Festival to raise funds for his non-profit organization, Stand Up & Learn, a program on Nantucket that teaches children how to do standup comedy.

“I teach kids, especially junior high school kids, to basically get up in front of people and tell a story, a humorous story,” explains Flynn.

“Whether they go on to use it to sell insurance or be a better dinner guest at a dinner party, we teach them the importance of being funny and storytelling,” he adds.

Born and raised in town, Flynn graduated from Daniel Hand High School in 1980. His mother, Catherine “Kitty” Flynn still resides in town, as do his two sisters.

“Fear of Heights” is a bow to his grandfather and father who toiled in New York City as ironworkers. He talks about the iconic photo, “Lunch Atop a Skyscraper,” of ironworkers eating lunch on a steel beam high above New York City.

“If you looked at the furthest to the right, that’s my grandfather, Patty Flynn,” Flynn explains. “So, he was an ironworker and my father was an ironworker and, I don’t think I was expected to be a third generation ironworker, but I talk about that as being what I’m from and who I am.”

It was here in town that he honed his skills as a soccer player. He continued his education at the University of Massachusetts Amherst, played professional soccer, and started graduate school in Boston.

Then he caught the comedy bug and “dropped out of grad school,” says Flynn.

His career took him to Los Angeles for a time where he appeared in comedy specials on NBC, MTV and A&E; and his film and television credits include “The Heartbreak Kid” with Ben Stiller, “Me, Myself and Irene” with Jim Carrey, “Osmosis Jones” with Bill Murray and HBO’s “Sex and the City.” His oneman show, Around the Kitchen Table, won Best of the Fest at the Boston Comedy Festival and at HBO’s prestigious U.S. Comedy Arts Festival in Aspen.

This career comedian writes all his own material.

“This is a one man and a one man is very different,” he says. “There are funny parts to it, obviously with my standup background, it’s also a story I’m telling about growing up in Madison, about the choices I’ve made in my life, the influences that my parents had on me.

“It’s sort like the story of what I’ve overcome or what my life’s been like,” he adds.

Whether he’s up on stage talking about the fun and frivolity of his life or the low points, Flynn is able to entertain his audience. It has a name, dramedy.

“I’ve had kind of a wonderful life and I think it’s just that there are moments that happen in anyone’s life,” explains Flynn. “One of the things that you do when you write one of these things is the shared human experience that all of us have, divorces and family members dying or getting cancer, whatever it is, all of us have our journey.

“It’s hopeful and uplifting. I hope it’s hopeful,” he says, with a laugh. Boris is excited to share her friend’s talent with others.

“I love Kevin and everybody does,” says Boris. “He’s always been a great guy and, of course, off the charts hysterical. So, it’s nice that we’re able to bring him in. We’re not a big venue, so it will be a very cozy, almost private performance.”