Cheyenne Jackson’s Big Gay Glow-Up: From “Delicate Cheyenne” to Broadway’s Boldest Himbo

Cheyenne Jackson knows a thing or two about near-misses and second acts. For every standing ovation on Broadway, there’s an audition that didn’t pan out. But as Jackson tells it, the heartbreaks and “not-meant-to-bes” have only sharpened his sense of purpose—and, crucially, his pride in being a visible queer artist in a world that hasn’t always welcomed authenticity with open arms .

“It was not meant to be, ” said Jackson, reflecting with refreshing candor on the high-profile roles that slipped through his fingers: the HBO series Looking, a star turn in the movie "Into the Woods", and more. “I used to take every rejection personally. Now I get it. If it’s not for me, it’s not for me. There’s freedom in that, you know? ” .

For Jackson, that freedom didn’t always come easily. In an industry notorious for its unspoken rules about how “out” an actor could be, he learned to compartmentalize, to butch it up, to keep parts of himself in the wings. “When I got into this business, there weren’t out gay actors who were actually successful. Not really, ” Jackson told Playbill in a recent interview. “I repressed my feminine side for a long time, I learned how to do the hyper-masculine thing. But there was another side of me, the other half of me, that’s very soft, very sensitive. That side is equally valid and real” .

It’s a journey familiar to many LGBTQ+ people, especially those who came of age before the current—if still imperfect—wave of queer representation. “I had so much internalized homophobia for so many years, ” Jackson confessed to Playbill. “But now, I am the most comfortable I’ve ever been in my skin as a dad, as a human” .

That comfort is hard-won, and it’s visible now in every move Jackson makes—whether he’s playing the “lovably dim” Sonny in "Xanadu," the dashing Sir Harry in "Once Upon a Mattress," or, most recently, the flamboyant Mary’s Teacher in "Oh, Mary!" .

The character of Mary’s Teacher, Jackson admits, is the “queeniest” he’s ever played. And he’s relishing every campy, heartfelt moment. “What made Mary’s Teacher a little scary initially has also made it liberating, ” Jackson said. “I used to not be that kind of actor. But I’m ready. This ‘new’ and more-authentic form reflects traits I got clocked for more than 20 years ago. There has to be something more” .

Jackson’s evolution isn’t just about the roles he plays—it’s about the life he leads. Married to Jason Landau and a proud father of twins, Jackson wears his queerness with the kind of ease that would have seemed impossible to him when he was coming up in the business .

“People that are perceived as stupid, there’s always a secret, ” he mused, explaining his unique approach to playing “himbo” roles. “As Marilyn Monroe used to say, the dumb blonde—she’s the one that actually knows the whole deal. She’s the one in control. Any part that I played where they’re actually stupid or not in on the joke, I always give them a little secret. It can’t just be that everything goes over their head. There has to be something more” .

And there is. In the queer community, “reading between the lines” isn’t just a survival skill—it’s an art form. Jackson’s nuanced, layered performances have made him a kind of queer icon for a new generation, one that demands complexity, authenticity, and a healthy dose of camp.

Recent years have brought Jackson not just professional highs but profound personal loss. The sudden death of his best friend, Tony winner Gavin Creel, in 2024 deeply shook him—and, in a paradoxical way, pushed him toward even greater authenticity .

“Gavin was my best friend for 22 years, ” Jackson told Playbill. “When he passed… just the idea that this is my one life. It put me past pretending, done being worried about pleasing those around me… I actually do not care what people think. For someone who’s spent their life worried if people like me, if I’m nice enough, if I’m sweet enough—I had to let that go” .

There’s something profoundly queer about that realization. For Jackson—and for so many LGBTQ+ people—it’s the understanding that life is too short for anyone else’s closet. That being “delicate” isn’t a liability, but a superpower. That the roles you don’t get can be as defining as the ones you do.

Jackson’s story is more than a personal narrative—it’s a call to action for anyone who’s ever felt the pressure to downplay their truth, to make themselves smaller, to fit in. Whether you’re a theater kid in the Midwest, a non-binary artist in New York, or a gay dad navigating PTA meetings, Jackson’s glow-up is a beacon.

“Something has happened to me in the last year and a half, ” he confided. “I am the most comfortable I’ve ever been in my skin. ” And he’s not alone. As more out LGBTQ+ artists take center stage, the message is clear: there’s room for every kind of story, every kind of voice—delicate, queenie, or otherwise. And that’s something worth singing about .