Avery Pearson knew something was up when Jeff Ross looked at him weirdly. The pair locked eyes at a comedy club in the fall of 2018, days after Netflix announced a new show, Historical Roasts, with Ross at the helm. Pearson, a budding comedic musician who’s always on the hunt for new gigs, debated whether or not he should pitch himself to his buddy Ross. In the end, he demurred – if it was meant to be, it would be.

The next day, Ross called him up. When they met in person, Ross casually offered Pearson the role of musical director of the show.

“He was basically asking me to do what I know how to do better than anyone else,” Pearson says over the phone from his home in Los Angeles.

It was the ultimate break for a nice Jewish kid from Toronto who’s spent years dreaming of making people laugh in L.A.

Pearson grew up in the Toronto suburb of Thornhill, where his parents forced him to play an instrument. He gravitated toward the piano, practicing “Hot Cross Buns” and “Havah Nagilah.” By high school, he branched out, combining music with comedy for the first time, covering Adam Sandler’s “Hanukkah Song” onstage for his school’s Christmas pageant. Show business was his calling. After university, he moved to New York, where he spent eight years in the theatre world, living the typical life of a struggling actor.

He wound up returning to Toronto, where he landed small gigs on Suits and The L.A. Complex. The latter was a short-lived primetime soap opera about a struggling Canadian actress who tries to make it big in Hollywood. After less than a year in Toronto, Pearson took a cue from the show and moved to California.

“You just want to see if you can do it at this level in L.A.,” he says. “I got drawn to the light of it. It felt very natural to be out here.”

He landed a doorman gig at the Hollywood Improv, one of L.A.’s most prestigious comedy clubs. He walked in with a whole new mindset: “I just shifted my life to try and have fun and be nice to everybody,” he says.

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Pearson never bothered the comics about potential opportunities. But there was a baby grand piano onstage at the club and sometimes, before the doors would open, he’d sit up there and play. One day, the manager overheard him.

“You’re good,” he told Pearson. “Stay up there.” So he did. The lighting operator flicked on the lights and the crowd filed in.

“Suddenly, I’m playing piano in front of 200 people at the Improv and I don’t know what to do,” Pearson recalls.

He became the club’s warm-up musician, playing before the night’s host walked on. That transitioned into his own weekly late-night show at the Improv, The 88 Show, where he’d hone his musical comedy skills before drunken late-night audiences.

After working at the Improv for a year, Jeff Ross, the Jewish blue comic who’s famous for roasting everyone from Justin Bieber to William Shatner on Comedy Central, walked onstage after Pearson finished his warm-up. Pearson was having a drink at the bar when a man ran in. “Where’s Avery?” he shouted. “Jeff wants you to go onstage.”

Pearson sat there, dumbstruck. “To do what?”

“Play piano!”

So Pearson scrambled back onstage. “Play something sexy,” Ross instructed. Pearson obliged, playing a classy jazz riff while Ross roasted a sucker in the audience. “Play ‘You Are So Beautiful,’ ” Ross said next, and Pearson, who’d never played the song before, had to figure out the chords on the spot.

“At first I was scared,” Pearson says. “There’s no job in the world – except maybe surgeon – where you know exactly how you’re doing in real time. You have to just be there, be present and listen.”

Since then, other comics have asked him to accompany them during their sets. He’s worked with Tiffany Haddish, Chris Redd and Dane Cook, both onstage and in comedic music videos he’s written and starred in.

Four years after Ross gave him his first big break, he gave him his second, offering him the role of musical director for Historical Roasts. The six-part Netflix series attracted global criticism for its roast of Anne Frank, though that episode resonates deeply with Ross himself – and Pearson, too. His Jewish roots have remained close to his heart throughout his career, specifically because of his parents, who’ve travelled to New York and L.A. to support him and catch his performances, no matter the form.

“Just by following the signs, following my path, I kept falling into it,” he says. “It culminated into this beautiful thing that I could have never planned.”