Star Kai Clifton caught in ‘A Strange Loop’

Meta-musical “A Strange Loop” tells the story of Usher, a Black, queer writer penning a musical about a Black, queer writer penning a musical about a Black, queer writer.

Actor Kai Clifton, who plays Usher in the upcoming Boston production of the show, is also a Black, queer writer.

“We’re extremely similar,” Clifton told the Herald of the parallels between actor and character. “There’s a strange loop within a strange loop for me here.”

Hold on, more loops are coming.

SpeakEasy Stage Company and Front Porch Arts Collective bring “A Strange Loop” to the Wimberly Theatre April 26 to May 25 after the show’s impressive Off-Broadway and Broadway run. Writer Michael R. Jackson’s work won the Pulitzer Prize in 2020 and two Tonys in 2022 including best musical. The success is even more impressive considering how outside the mainstream it is for a Broadway show — the action mainly takes place in Usher’s mind as the character acts as an usher at “The Lion King,” a job Jackson had for four years.

It’s the kind of success Clifton never thought they would see.

“It’s such a privilege to play a role that I can understand so well and whose identity is so specific to mine,” Clifton said. “I can’t help but think about all the people that came before me who identified with Usher but didn’t get to see their story told on stage.”

Despite being a veteran of musical theater and a star student — Clifton studied at Italy’s Assisi Performing Arts Program on a full scholarship — they had never seen a Broadway musical while it was on Broadway. But after coming across a promotional clip for “A Strange Loop,” they knew they had to make the pilgrimage.

“I remember sitting in the audience not knowing what I was getting myself into,” they said with a laugh. “After the show, after that rollercoaster of a feeling, I remember looking up at the marquee and saying, ‘I have to play this role. I don’t know where, when or how, but I know it’s going to happen.”

A Boston native, Clifton has made their name across New England in a range of venues. They have dug into drama as Sofia in “The Color Purple” and won the 2022 Broadway World Boston Award for Best New Play or Musical for writing “Queens,” about the lives of four queer Black men. They have made kids giggle and gasp as Ursula in “The Little Mermaid” and Gloria in “Madagascar.” What they haven’t done much of is sing in their natural voice.

“Recently, I’ve played a lot of roles in drag,” they said. “These are roles written for an alto, mezzo-soprano woman, and I can sing them. But Michael R. Jackson has written this glorious score for a pure tenor, which is so refreshing. These songs are truly beautiful, the lyrics so raw and honest.”

“This is not only a role that looks like me, but sounds like me,” they added.

Clifton knows not everyone will be drawn to the musical the way they were, not everyone will be looped in in the same way. But they are confident everyone will connect with Usher.

“You will find something that’s so relatable in this character,” they said.

For tickets and details visit speakeasystage.com

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