Craig Winberry brings George Michael back to Boston

When actor-singer-songwriter Craig Winberry would do cabaret shows, he always put some George Michael in the set.

Sometimes the Michael song came with some cheek — after returning from Carnival in Brazil one year, Winberry closed a show in a speedo and headdress singing Wham’s “I’m Your Man.” Sometimes it came with tender sincerity, such as the big ballad “One More Try.”

So when Winberry saw a casting call for something called “The Life and Music of George Michael,” he felt he’d been preparing for the audition for years.

“The summer of 2021, I’m having a horrible day, I turn on my phone and I see this casting notice,” Winberry told the Boston Herald. “I was like, ‘That’s me.’”

“It was like I’d already been working toward this project,” he added.

“The Life and Music of George Michael” went out in 2022 and built some buzz. By 2024, it had grown into a sensation — crisscrossing the States and Canada, touring Australia, selling out Boston’s Emerson Colonial Theater. The show returns for two performances at the Colonial on Nov. 1.

The show features two Michaels — Connor Antico covers the Wham era; Winberry takes on the more weighty solo stuff. As a longtime fan, Winberry understands that Michael’s legacy is nuanced, complex, and massive.

“That poppy, teeny bop sound was Wham,” Winberry said. “But George knew he wasn’t always going to be that 19-year-old bouncing up and down. He said, ‘I have other parts of my life that I want to show you.’”

That means this performance gives you bubble gum such as the irrepressible “Wake Me Up Before You Go-Go.” But it also dives into 1998 international hit “Outside” — the singer’s bold declaration of gay pride (and a hell of a dance jam).

“I grew up with (Michael’s music) so I understand it, especially some of the coded language,” Winberry said.

Winberry says he would never call himself an impersonator, but he and the band have an ear and eye for the icon’s meticulous approach to pop. Lyrically and musically, artistically and emotionally, nobody matured through finely-crafted Top 40 masterpieces like Michael did from Wham’s “Freedom” to “Faith” to “Freedom ’90” to “Outside” (all of which are in the show). Oh, and that band, half of them are Berklee alums with mighty chops.

Between tours, Winberry has made time for his own voice. Earlier this year, he released an album of his music, “Sidewalk Survival Guide.” And if you dig GM’s electronica-touched ’90s stuff, you’ll want to give it a spin.

“It’s for anyone who is on their way to somewhere else but still trying to find themselves,” Winberry said. “And there’s all types of music, gospel, a nice ballad, some bossa nova, there’s pop.”

(C’mon, how GM is all of that?)

When not spending time on his own stuff, Winberry is thrilled to bring this show to Michael’s ever-expanding fan base. No matter where you are on your journey, you’ll find something to dance to — and something to think about — at “The Life and Music of George Michael.”

For tickets and details, visit thelifeandmusicofgm.com