The Boston Comedy Festival, which kicks off May 16 with Todd Barry and two stand-up contests, features a lot of familiar faces this year. Headliners Jackie Flynn, Zach Sherwin, and Robert Kelly all spent their formative years in the local scene — as did Erin Maguire, who hosts a pair of stand-up contests. Joe List, the festival’s Comedian of the Year, and Brian Kiley, who’ll receive the Lifetime Achievement Award, have deep roots here as well. They’ll be honored at the festival’s closing gala, as will Topper Carew. Elsewhere, Shane Mauss previews his “A Better Trip” show, and scene staples Steve Sweeney and Juston McKinney both headline their own nights.
As a comedian who broke into the scene at a young age, List said news of his honor resonated. “I remember the Boston Comedy Festival started [in 2000] right around the same time I started. So it has sort of a special meaning to me. I remember [as] a teenager being like, ‘Oh, my God, we have our own festival. This is crazy.’”
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It has been roughly eight years since List has been part of the festival, and he returns with a lot less to prove. He released his first feature film, “Fourth of July,” in 2022, starring as an anxious jazz musician dealing with his family at a holiday getaway. He co-wrote it with Louis C.K., who directed. List is also one of the more prolific stand-ups in the country and has his third self-produced hourlong special, “Enough for Everyone,” slated for YouTube this summer. He’s also had the creative freedom to film a documentary about his friend, one-time Boston comic Tom Dustin, who now owns a comedy club in Key West. Tentatively titled “Too Funny to Hate,” it is expected to be released in the fall.
This time around, List, a Whitman native, won’t be competing in the stand-up contest — his resume speaks for itself. “It’s definitely a different vibe,” he says. “It’s nice to know I’m going there to win something as opposed to trying to earn my win. Definitely a lot less stress and anxiety this time.”
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Kiley, a Newton native, comes to town purely as a stand-up for the first time in decades. He was a writer on various incarnations of Conan O’Brien’s shows for 27 years and on “The Ellen DeGeneres Show” in its final season.
Kiley had been doing stand-up for about a decade when he got his break with O’Brien; while he’s still pitching scripts, he has been touring for the first time in almost 30 years. “I’m just doing stand-up,” he says, “and I forgot how hard it is. I mean, I’ve been doing stand-up all along. But I didn’t have to go on the road for 28 years.”
There was a daily routine associated with writing for television, and a normal gang of people he’d see every day. He misses the shared laughter of a writers’ room. “I was lucky that I got to work with such funny people for so long,” he says. “And now I’m spending so much time by myself. I’m not making myself laugh as much as I should be. I need to step it up.”
Kiley released an online special earlier this year, “. . . What’s His Problem,” under the Dry Bar Comedy banner. His stand-up has been featured on SiriusXM radio and he’s published two novels. But he is best known for his work as a writer, so receiving the Lifetime Achievement Award at his hometown comedy festival is a bit humbling — especially when he looks at the roster of previous honorees. “Everyone else is famous,” he says. “It’s like Jonathan Winters and Norm Crosby. So I’m sure people are gonna be like, ‘Who the hell is this guy?’ I might have to go out [and] just talk for a little bit and explain to them who I am. But I was certainly not expecting this. And I couldn’t be more honored.”
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Erin Maguire started performing stand-up less than 10 years ago, long after she had left Boston. But the seeds were sown here. An Arlington native, she joined a traveling improv troupe her sophomore year in high school. “I never told them how old I was because I was afraid I wouldn’t get hired,” she says. “So I just auditioned for it. And it was a paid gig. It was my first paid thing.”
She went to college for musical theater and spent some time straddling the improv and theater worlds before finally committing to stand-up comedy. “I think it’s true what they say about the 10-year mark in stand-up,” she says. “I feel like things are just starting to click or pop open.”
Maguire is a veteran of the stand-up competition and comes back to the area frequently — she’s been a regular at the BCF and the Women in Comedy Festival, and will be opening for Adam Ferrara at the Off Cabot in Beverly in June. At the festival, she’ll be hosting a preliminary round of the stand-up competition and closing round three. She enjoys networking with other comedians and showing off her hometown to her fellow New York-based comedians. “I just think funny people come from Boston,” she says. “I think it’s something in our blood.”
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BOSTON COMEDY FESTIVAL
May 16-20, various venues and ticket prices. www.bostoncomedyfest.com
Nick A. Zaino III can be reached at nick@nickzaino.com.