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Massachusetts native James Jackson Jr.’s head-spinning journey into ‘A Strange Loop’

James Jackson Jr. in rehearsal for "A Strange Loop."Daniel Vasquez

About a decade ago, James Jackson Jr. had largely let go of his dreams of Broadway stardom. After moving to New York City in his mid-20s, the actor, who was born in Boston and grew up in Randolph, eventually carved out a theater career doing musicals like “Smokey Joe’s Cafe,” “Dreamgirls,” and “Ragtime” at regional theaters and performing in various downtown and fringe shows around the city. But he had tired of casting agencies pigeonholing him, making degrading comments at auditions, or ignoring him altogether. After he was let go from his job performing with the “Radio City Christmas Spectacular,” Jackson knew it was time for a transformation.

Filling in on a friend’s cabaret show one evening, a “lightbulb” went off as he crooned a Carole King song and bantered with the audience. He decided to pivot, developing a solo cabaret act that he has performed in New York, Cambridge, and other cities.

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In between gigs, though, something else was brewing. He was helping a friend, Michael R. Jackson, develop an unconventional musical inspired by Michael’s own life, centered on the inner life of a Black, queer theater writer creating a musical about a Black, queer theater writer. James Jackson, who plays one of the six nagging Thoughts inhabiting the character’s psyche, says he never imagined that his friend’s transgressive, meta musical would get produced at all, let alone on Broadway. But then the unexpected happened. “A Strange Loop” went on to win the Pulitzer Prize, five Drama Desk Awards, two Obies, and, this month, the Tony Award for best musical.

Jaquel Spivey (center) and the cast of "A Strange Loop" perform a song from the show at the Tony Awards at Radio City Music Hall June 12.Theo Wargo/Getty Images for Tony Awards Productions

“When I first moved here, the goal was to be on Broadway,” says Jackson in a Zoom interview a few days after the Tonys. “But then I never thought that anything like this would happen at this point. I had sort of stepped away from musical theater in a way. But now here I am making my Broadway debut at 46 years old. Everything that is happening is so surreal.”

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Indeed, he’s trying to “savor it all,” he says. On opening night, he met Andre DeShields and told the theater legend: “Because of you, I am able to be my full self onstage, I can be as gay as I want, as me as I want, because when I was little I saw something in you, and I was like, wait, he’s a little weird, too — kind of like me.”

At the dress rehearsal for the Tonys, Jackson ping-ponged into a gauntlet of theatrical heroes. Ben Vereen told him and “Loop” costar John-Andrew Morrison that they were changing the face of Broadway. He bumped into Bernadette Peters, already wearing her sparkly gown for that night, and she asked if he wanted to take a picture with her. “I thought I was going to melt into the floor,” he says.

He really lost it, though, when he met Whoopi Goldberg — and cried on her shoulder — after she came to see “Loop” at the Lyceum Theatre, the home of her breakthrough 1984 solo show that was filmed for television. “I was trying to tell her how much she has meant to me and how I used to recite her entire one-woman show when I was 10 years old. I was hugging her, and I started to break down.”

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Just then Jennifer Hudson, who’s on the “Loop” producing team, came over and put a hand on his arm to console him. “I was like, ‘What the hell is my life right now?’ ” Jackson says.

Indeed, it’s been a long journey from his years growing up in Randolph. Jackson remembers choreographing dances in his basement to the “Flashdance” finale, memorizing “Muppet Show” jokes, and putting on shows for his parents. His mother, Geraldine, who worked as a cancer researcher at Boston Children’s Hospital, was a piano prodigy, so James took piano lessons from the age of 5. (James Sr., a business owner, still lives in the actor’s childhood home.) At Randolph High, Jackson got caught smoking and singing in the bathroom and was offered a choice: Either go to the principal’s office or join the music department. He chose the latter.

His high school chorus teacher, Lynne-Marie Dandeneau (nee Sylvia), helped foster his talents. “I would not be doing anything even remotely close to this if it wasn’t for her. She came to see the show, and we stood out under the marquee and just cried,” Jackson says. “Everyone who’s known me all these years is like, ‘We’ve watched how hard you’ve worked and how you’ve taken control and done your own thing.’ ”

James Jackson Jr. as Thought 2 in "A Strange Loop."Marc J. Franklin

Morrison, the Tony-nominated actor who plays Thought 4, has been working on “A Strange Loop” with James Jackson for well over a decade, so he’s witnessed his friend’s invaluable insights during the show’s development. “I’ve seen him ask questions that have shifted whole moments, that have refocused scenes,” Morrison says. “No one has a quicker wit. He can break your heart with a soulful song and then in between make you wet your pants with a joke.”

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As Thought 2, Jackson plays the voice of lead character Usher’s “Daily Self-Loathing.” At times, that includes embodying Usher’s loving, devout mother who also fears for her gay son, or a sexually liberated doctor who encourages Usher to get his freak on, or an exaggerated Harriet Tubman. As the show goes on, Jackson tries to imbue his character with a healthy skepticism that’s more protective of Usher than mean-spirited.

Not only must Usher come to accept himself and his flaws, says Jackson, but he has to find a way “to fight for his right to live in a world that chews up and spits out Black queers on the daily” — a journey with which Jackson says he can identify.

“I was 23 once, so I’ve been there,” he says. “But I’ve been through a lot of therapy and I’ve worked on myself a lot. So I’m not in the same place as Usher, but I can relate to him and can draw on some of my experiences.”

He believes the show is connecting with audiences because everyone experiences self-doubt and struggle at some point in their lives and “everybody has a family, and they’re all messed up,” he says with a laugh.

Still, because the author and his actors doubted “Loop” would ever get produced, let alone wind up on Broadway, Jackson says that freed them from any creative constraints. They never worried what people would think about some of its more explicit, troubling, or brutally honest moments. “I think it changes the way you work,” he says.

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Indeed, Jackson says he felt that same sense of liberation when it came to his “absolutely rewarding” move into the cabaret and concert world. “I have a confidence now. I spent all this time trying to fit into a certain box or trying to be other people. But then I started to go in and be like, ‘Oh, I don’t give a [expletive]. I’m going to sing what I want to sing.’

“And it changed the way that I walked into auditions and into those spaces, and they were finally like, ‘Oh, OK, we see you.’ There is a way in as yourself.”

Christopher Wallenberg can be reached at chriswallenberg@gmail.com.