The Chutzpah Festival is always good for a laugh. This year it comes in the form of two accomplished standup comedians stepping outside the box with a couple of standout one-person shows. Judy Gold answers 25 Questions for a Jewish Mother and Brad Zimmerman serves up My Son the Waiter, a Jewish Tragedy.

Zimmerman’s story is a testament to stick-to-itiveness. The man moved to New York from his New Jersey home to become an actor in 1978. He took acting classes, anyway. For years. Did a couple non-union commercials and nonpaying one-man shows but that’s about it, making his rent by working as a waiter. In 1996, he took a comedy class, where he really found his voice and a bit more success. It didn’t stop him from his restaurant work, though.

In fact, it wasn’t until 2007 that he finally hung up his apron, two years after beginning work on his latest creation. And it wasn’t until last year that he signed with a manager and sold the show.

“I’m really bearing the financial fruit of the piece now,” he says on the phone from Florida. “So that’s after nine years. It doesn’t matter. It takes as long as it takes. It’s been a real uphill battle but at this point I feel like I’m warming up. And that’s kind of an interesting feeling. I’m the late bloomer’s late bloomer.”

He calls the play a “hybrid: part standup, part theatre”. He incorporates the great stories he developed for his stand­up act about serving food for a living, which became his signature bits, allowing him to open for the likes of George Carlin, Joan Rivers, and Brad Garrett. The only difference now is that he doesn’t have to be so punchline-heavy in his delivery, although the anecdotes are still hilarious.

“It’s not just funny; it’s very moving,” he says. “When I go out on stage to do the one-person show, I don’t feel the kind of pressure to get the laugh. Which is huge.”

Many performers are loath to ever bring up the dreaded day job for fear of looking like an amateur. Zimmerman never cared.

“I wasn’t concerned about people thinking I’m not professional,” he says. “It probably bothered other comics who advised me more than me. It never bothered me. If you’re good, you’re good. I don’t care if you’re a truck driver during the day: if you’re funny, you’re funny.”

But there’s more to the evening than waiter stories. That just sets the table, so to speak, for exploring how he’s struggled in show business. He talks about growing up, his social life (or lack thereof), reality television, and his mother, among other things.

Obviously his life isn’t a real tragedy, even if it sometimes felt that way for his mom.

“When you think of Jews, you think of lawyers, doctors,” he says. “That’s their idea of success. It’s all about money. So if I’m waiting tables for 20 years and not making a dime….Naturally, that’s in a sense the tragedy, that I’m not this multimillionaire who the mother can brag about. I’m this waiter.”

Now with tour dates all over North America, Zimmerman can exhale a bit.

“It’s the first time in my life that I’ve never worried about money. I can’t even tell you what that’s like,” he says. “It’s beyond heavenly. It’s amazing. I’m exactly where I should be. I don’t think I should have my own sitcom….I’m very content doing this and seeing how far it takes me. It’s kind of a challenge, and it’s kind of thrilling in its own way.”