BENNINGTON — For one night only, comic actor Dion Flynn will perform his one-man show, "The Only Brown Kid in the Trailer Park," at Oldcastle Theatre on March 25.

Since Flynn was little, his earliest skill was storytelling, his mother told him. He told made-up stories, complicated ones and real ones. Once he encountered a troubled childhood, and even as a young adult, Flynn realized that humor was his key to surviving.

"It's a solo show with ups and downs and has a message of hope," Flynn said, "but before that there's some difficult subject matter which is dealt with using humor and the skills of story telling. Going through what felt like such a unique and painful childhood, it gave me a lot of what I had to say. People tend to listen longer if you give them insight and laughter."

Most known for his President Barack Obama impression and features on Late Night with Jimmy Fallon, Flynn received a Bachelor's degree in theatre and a Master's degree in acting from New York University, according to his website. He also has taken part in Moth Storytelling events, Shakespeare in the Park, The Public Theater and The Guthrie, and is the latest member of New York City's Big Black Car longest running improv.

The comic actor's relationship to the Obama character stemmed from peer suggestions. After studying the president's voice for a weekend, Flynn nailed it. However, he's yet to meet the nation's leader, but said he foresees it happening.

His 3-year-old son still can't tell the difference between parent and president, Flynn said.


Flynn is the only artist alive to have worked with both Spike Lee and Rosie O'Donnell.

On Friday, attendants should expect a story about a biracial man's journey in a trailer park 40 miles south of the Mason-Dixon line to the White House. The show will present universal themes of addiction, individuality, relationship navigation and alienation.

"I was always laughing and dealing with life with laughter and that's what my show is about, using humor to get through to the intense feeling of being all alone," he said. "I grew up the only brown kid in the trailer park. That's why I felt alone on the surface, and I thought it was just me that felt that way. I was all by myself, but come to find out as I got older and talked to people, I found that everybody else felt that way too."

In addition to Obama, audience members will witness more than 20 characters during the 90 minutes autobiographical show.

"The Only Brown Kid in the Trailer Park" has only been performed eight times in New York City and Upstate New York. Flynn will perform at Oldcastle on Friday and then at Bennington College the next night. He said he's looking forward to speaking to younger folks.

Comic actor Dion Flynn, who has been featured on Late Night with Jimmy Fallon, will perform his one man show, "The Only Brown Kid in the Trailer
Comic actor Dion Flynn, who has been featured on Late Night with Jimmy Fallon, will perform his one man show, "The Only Brown Kid in the Trailer Park," on March 25 at the Oldcastle Theatre. (photo courtesy of oldcastle theatre)

"I went through struggles at some point and if I didn't carry on I wouldn't have a family and career for this silly impersonation I do," he said. "When people are young they get to a point they want to give up, and that's how I felt."

Flynn adds a question and answer portion to the end of his shows and typically people will come up to him and share their stories. One woman told him that she would reevaluate the assumptions of how she saw her child process things because of what he said during his show. The woman explained that there were things her child was scared of but she didn't think they were scary.

"Ultimately it [humor] has made it so I could survive a lot of difficult and challenging things," he explained. "I did drugs but I've been sober for 19 years and that's part of the story. I was down and depressed and almost gave up the whole thing. I had to deal with racism in the South growing up in the '70s and I just navigated it."

The show begins at 8 p.m. and tickets are available at

— Makayla-Courtney McGeeney can be reached at 802-447-7567, ext. 118.