fb-pixel Skip to main content

Comedian Will Smalley took one big step, and then another


Age: 33

Hometown: Brockton

Think of: He has the “normal guy” likability of Mike Birbiglia or Dwayne Perkins.

What caught our eye: His cool wit, and his ability to collaborate and improvise at Ken Reid’s old “Secret Menu” show at the Comedy Studio.

Light bulb moment: Smalley started keeping what he thought was a comedian’s notebook at 19 as a student at Emerson College. But it wasn’t until after he came out as gay in his 20s that he got the courage to go onstage and try comedy. “Once that happened, everything else seemed a little less unattainable,” he says. “Comedy is something that I had always loved and revered and wanted to do.”


Biggest thrill: Performing at the Bridgetown Comedy Festival in Portland, Ore., in 2014. “There was a gay show we did that was just super fun,” he says. “I met a lot of great people, and the festival itself was top-notch.”

Biggest surprise: Getting to call himself a comedian in a town full of comedians he admires. He’s gotten advice from veterans like Tony V and been treated as a peer by people like Reid. “You’re friends with these great performers you’re in awe of.”

Inspired by: He loves what he calls “weirdos.” A friend once asked him to make a list of his top people, regardless of medium. “They were all people who were breaking form, like Carlin, Mondrian, and Voltaire,” says Smalley. “It sounds a little pretentious, but those are my people who I was inspired by in school and later in life and early into comedy.” But he also loves silliness, which is why he’s a huge fan of Brian Regan. “I don’t know if there’s any comedian that makes me laugh more.”

Aspires to: Smalley would love to be able to leave his day job at an investment bank and make a living as a comedian, but he also appreciates what he’s able to do right now. “I’ve been afforded being around these lovable weirdos and getting to do all these weird shows and festivals and travel,” he says.


What people should know: “A lot of people, it feels like they hate and love this life, but I love doing it. I love the power of making fun of who I am when I want to, and the power of being proud of who I am when I want to be. I like to have a voice in the comedy scene and the gay scene, and have those two be the same thing.”

Coming soon: Smalley cohosts “Two Kids in a Trench Coat” the third Wednesday of every month at the Milky Way Lounge in Jamaica Plain, and he’s working on a podcast of the same name. He may do more variety shows in partnership with burlesque performer Ginny Nightshade, like the show the pair hosted this month at the Middle East. In September, Smalley will return as the announcer for “Old School Game Show,” which will host a Halloween edition at Oberon.

Links: On Twitter @WillSmalley

Nick A. Zaino III can be reached at nick@nickzaino.com.