9-year-old comic finds success on the streets of Annapolis

Cool Kid Leo WAccording to his mother, Leo Braley didn’t say a word until he was 3 years old, but he’s been making up for that silence ever since.

On Wednesday evenings this summer, you can see — and hear — just how far Leo has come at the weekly Dinner Under the Stars festival on West Street in Annapolis.

Since mid-June, the Annapolis native has been regaling the crowd at the outdoor event with his jokes. Stand-up comedy seems an odd gig for a 9-year-old, but not to those who know him best.

The youngest of three children, Leo is the funny one in his family, they say. He’s a talker and a joker, with expressive eyes and a charming smile, and while he had never done stand-up before a crowd of strangers before, it’s been a natural fit.

“He’s that kind of kid,” says his mother, artist Stacey Turner, who runs the West Street gallery and classroom ArtFarm with business partner Alison Harbaugh. “He’s never been afraid to talk to people or be entertaining.”

Leo got his public start as a jokester last summer, when he stood outside his mother’s shop giving away Popsicles to attract customers. He decided to toss in jokes at a dollar a pop.

Katherine Burke, a friend of Turner’s who runs the Annapolis Collection Gallery a few doors down, caught Leo’s act and suggested he try a more formal gig this summer, complete with a microphone.

She knew it would work. “I don’t know what it is about Leo,” Burke says. “He’s not shy, but he’s not rude; he’s not obnoxious. He’s just amazing. He’s Leo.”

Leo’s mother says business is booming. One night last year, she says, he pocketed $56.

“Some of the jokes are really bad,” Turner says. “It’s his embellishment that gets people laughing.”

As if to prove the point, Leo tried out one of his jokes in his mother’s gallery on a recent Wednesday, before he hit the streets. “People tell me I’m condescending,” he said, then added in a pitch-perfect patronizing voice, “That means you talk down to people.”

Mediocre joke, terrific delivery.

“I like telling jokes,” Leo says. “A joke comes into my head and I just tell it.”

He admits to no nervousness and, indeed, exhibits none, whether talking to a reporter or telling jokes in front of strangers. At the first Dinner Under the Stars this year, he borrowed the microphone used by a guest violinist, perched on a seat in front of Burke’s gallery, and reeled off jokes with aplomb.

“It was beautiful,” his mother says. “He just started being silly in front of people, and people loved it.”

Does he see a future in comedy? “It’s not the thing I had in mind,” he says. “But now that I actually do it, I see how much I like it.”

Asked if he thought he could make a living at it, he nods. “Yeah, I could.”

You might want to catch his act on West Street — before his rates go up.

By Pete Pichaske