Christine O'Leary: Comedy through truth telling

Ridgefield is fast becoming Connecticut’s Comedy Central due to the presence of a bigger than life comedienne, Christine O’Leary.

With an outrageous laugh, electric smile, and totally engaging personality, O’Leary has, in the last four years, changed more than 150 would-be comics into stage-ready performers who can pack the Ridgefield Playhouse.  

Giving 10-week comedy sessions throughout the year at the Playhouse, O’Leary has not encountered a student whom she has mentored who can’t take the stage and gets laughs with his or her own true-life stories.    

“It is not about telling jokes,” explained O’Leary, “it is about telling the truth, solving a problem and linking to your feelings and those of the audience. When you are on stage there is usually a brick wall in back of you and this is because you are simulating an assassination. You have two choices. You can kill or die. I show people through honest feedback, from myself and other students, how you can kill almost every time.”    

To get students into writing comically, O’Leary has devised her own curriculum based on the Rip and Read system. During the week students write freely about anything that comes to mind that might be funny. Then, when they come to class, they choose a portion of their writing to share orally. Students audiotape this chosen reading and circle the portions where there are laughs from the audience. Students then link these circled, laughable aspects into their beginning five-minute performance segments. This format is almost foolproof when you have O’Leary along as your support system.  

According to Gina O’Connell, who has taken the class numerous times, “Christine makes it so you will never fail or make a fool of yourself. Working with her is all about success waiting to happen.”

Sue Ellen Sprock Landwehr echoed O’Connell.

“Christine knows how to empower people to find their true voice,” she said.  

When asked when her performing talent was first recognized, O’Leary said,” I think I came out of the womb ready to perform. My parents, both from Ireland, were like amateur vaudevillians.  They were always singing and dancing and telling jokes. They said they were not surprised that even as a toddler, when I saw a plate of giant cashews on the table, it meant guests were coming, get your act together and make the living room into a stage.”    

“As I got older,” she said, “I began to direct others and perform in anything and everything. When I really knew I was destined to perform, however, was after a performance of Rockin’ Robin. After rockin’ the house, I got a high I had never experienced before. From then on it was, Get me to anything that simulated a stage and let there be at least two in the audience.”    

“At one time,” she said, “I even rented out the cellar of this old building in Algonquin, Maine, and made it into a theater. Then I wrote, produced and directed my own one-woman show, called Jump and You Will Grow Wings. Before the show I would stand in the public square in outrageous costumes with music and market the show. Next I would go to the theater, sell tickets, hand out programs, work on lights and sets, and act as a janitor. It was truly a one-woman show and I actually did quite well. Sometimes I only had two or three in the audience, but sometimes I had a sold-out house of 42.”  

Being a realist, however, O’Leary knew that she needed another career to pay the bills, so she chose to get a degree in social work and worked in many capacities in that field.

“Since I am a very caring and empathetic person, social work was a great job for me, but I still had to constantly perform on the side. I was a little discouraged until I entered a major comedy competition in Portland, Maine, in 2000. There were over 100 comics in the competition, very few women, and I was named the Funniest Person in Portland. Later on I moved up to being named one of the top 50 lesbian performers in the country and lost my job as a speaker for the Red Cross because I had been outed.”


Unlike most comics who focus on just getting laughs, O’Leary focuses on building a comic community, personal mentoring, bringing comedy to places where comedy is not usually found, and showing the power of laughter that can come from everyday stories from regular people of all ages and backgrounds.  

For O’Leary it is always “game on,” as she advises her protégés to play it big and own it. With no better role model than herself, both students and audiences come away smiling, thinking about how they should be better able to laugh at their own true-life situations, and just wanting more of the same.  

According to Laura Isler, who rarely misses a class, “Christine’s classes are cheaper, better and more fun than therapy, and everyone needs therapy.”