McCurdy's Comedy Theatre is, hands down, Sarasota’s laugh hub. The club has seen names like Sinbad, Kevin Nealon and Andrew Dice Clay take the stage. But in a pivot, McCurdy's will welcome Broadway actor and singer Chester Gregory for a one-time, Motown-themed performance at Music Mondays, a new weekly series at the downtown venue.

The Motown song lineup, which will include songs like My Girl and Stand By Me, comes naturally for Gregory.

“I feel as though I’ve sung these songs as much as the Motown legends themselves over the course of my career,” he says.

He channeled Jackie Wilson in The Jackie Wilson Story when he played the starring role at New York's Apollo Theater and received rave reviews from the New York Times in 2003.

That same year, he sang Lonely Teardrops, originally performed by Jackie Wilson, for Michael Jackson, who gave him a standing ovation. (Both were from Gary, Indiana.) When Jackson was leaving, Gregory says, “I ran up to him and pointed out how we were both influenced by Jackie Wilson." The late King of Pop stayed to talk and pose for a picture.

Gregory went on to produce and star in a look into the life of Jackie Wilson called The Eve of Jackie, which dives into Wilson's last performance in September 1975, one night before the Motown star collapsed on stage. Leading roles on Broadway include Dream Girls, Sister Act, the role of Seaweed in Hairspray and Motown the Musical.

In Motown the Musical, he played the lead role of Berry Gordy (the founder of the Motown Record Corporation), and was hand-picked by Gordy himself after Gregory's audition in 2015.

“There hadn’t been many portrayals of Gordy," Gregory says. "If any, they were stiff executive types. I portrayed him like he was an uncle from the Midwest who knew how to deal with kids from the projects. Diana Ross, Marvin Gaye—that’s where those artists were from. Gordy had to wrangle those personalities in. Approaching [the performance] as if he was a relative, with love, worked and he caught onto it.” 

At the upcoming Sarasota show, Gregory says that he'll get the chance to share stories between songs about "working with these legends."

A resident of Los Angeles, it won’t be Gregory's first foray into Sarasota. In 2014, he performed The Eve of Jackie at West Coast Black Theatre Troupe's 15th-anniversary gala at the Van Wezel Performing Arts Hall.

Three years later, he was invited to do it again for a packed house at the Sarasota Municipal Auditorium.

This time, at McCurdy's, we’ll get to see him up close and personal in the roughly 200-seat venue, for more of "a shared experience,” he says.

He'll be backed by a four-piece band and joined by a couple of surprise guest artists.

As for what's next: amid TV film projects and touring, Gregory is working on the visuals for his latest album, called Retrograde, which is “a fusion of soul, throwback and modern influences. It's a bit electric, and sounds like alternative soul,” he says. Download it here.

Music Monday at McCurdy's Comedy Theatre with Chester Gregory is April 17, at 7 p.m. Tickets are $30. For purchasing info, click here.