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Jimmy Dunn’s journey from surfing to standup

It happened to Jimmy Dunn. He'd worked at the Boston Garden as a teenager, installed bindings at a ski shop, dropped out of a couple of colleges (one in Hawaii, where he sharpened his surfing skills), then gone to work in a bank. In his early twenties, just for the heck of it, he decided to try his hand hosting at a comedy night in town. That led to a few more standup gigs, one of which delivered that life-changing moment.

Was there a moment in your life when you knew—once and for all, without a doubt, case closed—what you wanted to do for a living?

It happened to Jimmy Dunn. He’d worked at the Boston Garden as a teenager, installed bindings at a ski shop, dropped out of a couple of colleges (one in Hawaii, where he sharpened his surfing skills), then gone to work in a bank. In his early twenties, just for the heck of it, he decided to try his hand hosting at a comedy night in town. That led to a few more standup gigs, one of which delivered that life-changing moment.

“I remember it vividly,” Dunn says. “There was a [comic] in the back. He was complaining that he hadn’t had a night off in ten nights.”

Dunn listened to the grumbling carefully, in part because he possessed what might be called insider information. “I knew how much he was making because I was doing deposits at the bank. And quickly I calculated—in ten nights, this guy’s making more money than my old man makes in a month. And that’s when I went, this is a job, this is a profession. And that was the moment when I went, I’m going to do this.”

He did. Dunn drove all over New England, putting 80,000 miles on his car in a year, going to any venue that would allow him to perform and sharpen his standup, sometimes for $50, more often for $25, occasionally for nothing. Twenty years later, he’s one of the top comedians in New England, a performer who has worked in China, the Caribbean, Alaska, not to mention all over the rest of the United States.

Any regrets about that decision to ditch banking for standup? The answer comes with no hesitation. “Oh, it’s great,” he says of his job. “It’s the best.”

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