Cheyenne Jackson is not naïve—he knows what he brings to the table. “Much of my career, my lane has been the hot, dumb guy,” he tells us confidently. “I’ve perfected the character.”
And he’s not wrong. Jackson burst onto the Broadway scene as the Elvis-modelled Chad in 2005 jukebox musical All Shook Up. He then returned two years later as the lovably dim Sonny in Xanadu. He’s played similar roles on screen, making it his calling card across all mediums. And frankly, guys and straight ladies alike have happily taken in the view.
Now, Jackson is back on Broadway at the Lyceum Theatre; he plays Mary’s Teacher in Cole Escola’s wild hit comedy Oh, Mary! The casting seemed more than apt when news of it dropped, for no small part because Jackson's Oh, Mary! costume features a very tight, body-hugging set of trousers. It didn’t hurt that the casting has him re-teamed with his former 30 Rock co-star and foil Jane Krakowski (as Mary Todd Lincoln).
And yet, Jackson says, he balked initially when Tony-winning director Sam Pinkleton called to offer the role. “’You really think I can do that?' I said to him,” Jackson remembers. “I’m saying this with no false modesty—I wasn’t saying that so he would hype me up.” (“I’ve never been more sure of anything,” he remembers Pinkleton responding.)
The reason for that insecurity, Jackson says, is that as (proudly) stupid as Oh, Mary! is, Escola’s whacky comedy works—and has specifically worked through several rounds of replacements—because it’s stupid in a remarkably smart way (“Comedy is serious business,” Jackson shares, quoting comedy legend Tina Fey). Jackson had seen the play early in its Broadway run, catching a performance as he prepared to do a Los Angeles La Cage aux Folles with Pinkleton. He says he was amazed at how downtown and edgy and smart it was—and he found his focus completely on Escola, the play’s original title star (Escola won a 2025 Tony Award for the performance, no less).
But any qualms were just foolish insecurity. Over the years, Jackson has learned you have to have something behind the eyes, even when playing idiots.
“I think people that are perceived as stupid, there’s always a secret,” he reveals, glint in his eye. “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, it bears mentioning (without venturing into spoiler territory) that with Oh, Mary!, it's all intentionally absurd and silly. Jackson’s role is, arguably, more silly, foolish, naïve. But he is not dumb; he's hiding an explosive secret under his sleeve.
But what is unarguable is that Mary’s Teacher is supposed to be very hot. Mary’s response when he makes his first entrance? “Fuck.” And that means casting director Henry Russell Bergstein is tasked with finding actors to play the role that can inspire similar interior monologues in each night’s audience. “I’m so happy that even at my age, people want to see it,” Jackson says humbly. That might be putting it mildly.
Of course, being famous for being beautiful might seem like absolutely champagne problems. But, Jackson tells us vulnerably, it can create trouble. He didn’t get into the biz to be a piece of meat, but early in his career it was clear that his looks were his strongest asset, at least to some theatregoers and critics.
“I used to be very hung up on photo shoots,” Jackson remembers. “And I had a side. I would only be photographed from the left, because some photographer told me one day that’s my side, and I should never do the right. I got in my head.”
So, what’s different now? “Something has happened to me in the last year and a half,” he says, growing uncharacteristically serious. “To be honest, it’s since Gavin [Creel] died.” The Tony-winning actor, one of Jackson’s contemporaries, died suddenly at the age of 48 in 2024 from a rare form of sarcoma. The tragedy left much of the Broadway world reeling, Jackson included.
“Gavin was my best friend for 22 years,” he says soberly. “I don’t have that many friends. He was a tried and true. And when he passed… just the idea that this is my one life.” Jackson says the tragedy put him past pretending, done being worried about pleasing those around him. Since Creel's death, he’s been laser focused on being his complete, nuanced self. And unbothered by what anyone else thinks about it.
“I am the most comfortable I’ve ever been in my skin as a dad, as a human,” Jackson says (he's the father to twins with husband Jason Landau). “I used to read everything about me—comments, reviews, message boards. I used to read horrible things about myself, and it would just devastate me. The last few shows I’ve done, I have not read one thing. I actually do not care. 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.”
That, he says, even played out in the photo shoot for this very feature in the Playbill photo studio. “You can shoot me from any angle. I have a little love handle on this side that sticks out,” he remembers telling our photographer and photo editor, Heather Gershonowtiz. “I’m still vain, sure. Do I still want to look handsome—sure! But it’s not an obsession like it was.”
No surprise, that plays out in his performances, too. It’s what helped him say yes to Pinkleton when he called about Oh, Mary! even though he hadn’t initially thought that the part was for him—“What I’ve learned in my 50 years on this planet is when somebody, an artist that you respect, sees something in you that you don’t necessarily see in yourself, listen to them,” Jackson says.
What made Mary’s Teacher a little scary initially has also made it liberating. Again, without getting into spoiler territory, Mary’s Teacher has Jackson being, for lack of a better descriptor, queenier than he’s historically been in his career. “I had so much internalized homophobia for so many years,” Jackson says. “And when I got into this industry, there weren’t out gay actors that were successful, not really. 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.”
That freedom, Jackson says, has made him feel infinitely more free as an artist and actor, too. And that’s playing out eight shows a week at the Lyceum in Oh, Mary! “It’s a very malleable performance,” he reports. “When I go on with [understudy] Hannah [Solow], it’s a totally different Mary, and it makes everything a totally different vibe—and so Mary’s Teacher is completely different. I used to not be that kind of actor.”
Jackson has finally reached what he says is his most realized form, which is saying something with a career as storied and successful. Not only is Oh, Mary! offering him a chance to be maybe the most varied version of himself onstage yet, he's got another performance on the calendar where he'll be, arguably, even more vulnerably himself—a Carnegie Hall solo debut December 8. He's set to be joined by some fancy friends like Oh, Mary! co-star Krakowski and Hell's Kitchen's Jessica Vosk. But for the most part, the performance is kicking off a tour that forces him to be unapologetically Cheyenne for thousands of people, with no characters to hide behind.
But he's ready. He says that, though he's tried to project otherwise, this "new" and more-authentic form reflects traits he portentously got clocked for more than 20 years ago. He was co-starring with Tyler Maynard in Altar Boyz, a satirical Off-Broadway musical about a hilariously religious ‘90s-style boy band, in its 2004 world premiere at the now-defunct New York Musical Theatre Festival. During rehearsal, Jackson shares, Maynard gave him the nickname: “delicate Cheyenne.” That comment put him on guard at the time.
“Right off the bat, he had my number,” he remembers. “He saw me immediately.” Luckily, Jackson is game to let all of us see the real him now, too.
Cheyenne Jackson
Cheyenne Jackson
Cheyenne Jackson
Cheyenne Jackson
Cheyenne Jackson
Cheyenne Jackson
Cheyenne Jackson
Cheyenne Jackson
Cheyenne Jackson
Cheyenne Jackson
Cheyenne Jackson
