The reason why Cole Escola's show Oh, Mary! has found success at Broadway's Lyceum Theatre isn't solely because it's the perfect catnip for queer audiences, but the casting changes for each role have been pitch-perfect each time. Every new actor who takes on this production an absurdist take on the events leading to the assassination of Abraham Lincoln brings something new to the show, inviting audiences back to see it in repeat viewings. In the latest iteration of the play, 30 Rock alum Jane Krakowski is donning the bratty curls of Mary Todd Lincoln opposite her fellow sitcom actor Cheyenne Jackson, who is taking on the role of Mary's Teacher (a.k.a. John Wilkes Booth) from now until January. The part a teacher for the first lady with ulterior motives was originated by James Scully.Jackson is a devilishly handsome actor who cut his teeth on stage in shows like Thoroughly Modern Millie, Aida, All Shook Up, and more, before appearing on television shows like Glee, Ugly Betty, and Curb Your Enthusiasm. He is no stranger to the stage and took on the role of Sir Harry at the New York City Center production of Once Upon a Mattress last year. Before that, he joined the Into the Woods company as the Wolf/Cinderella's Prince at the Hollywood Bowl in 2019 and returned to the roles for his late friend, Gavin Creel, when the show was revived on Broadway in 2022. It took him a while to find the right show to return to Broadway for, but when the show's Tony-winning director, Sam Pinkleton, called to offer him a role in Oh, Mary!, he and his team immediately knew he had to say yes. (L-R): Cheyenne Jackson and Jane Krakowski in "Oh, Mary!"Emilio Madrid"I've flirted with coming back to New York many times, at least once or twice a year," Jackson tells Out. "I still get asked to come back and do Broadway shows, but nothing has been enough actually to let me leave my kids for this long." He goes on to say that he's a particular type of performer, and he sees himself as very malleable. Still, if he were to sink his teeth into a new role, he needs it to be in a show where he can "show all your crayons in your crayon box." And there's no doubt the actor used a handful to create his version of the part.Jackson said he worked with the show's director to map out his iteration of Mary's Teacher. "We wanted him to look like a horny Disney character I wanted the pants to be a little tighter than I'd seen and I wanted him to be a little more physically in your face, so that when there's the unravelling later, it can be all the more shocking," he said. The actors are given free rein to add some new physical elements (which Krakowski does not skimp on) and a few quips. The production team gave them the parameters for the scene's blocking (where the characters move and end up), but Jackson says, "As long as we say the words, we can do what we want." Jane Krakowski as Mary Todd Lincoln in "Oh, Mary!"Emilio Madrid His contemporary and friend, Michael Urie, was the last full-time person in the role, and he left Jackson with a word of advice: Learn the Shakespeare parts right away. As some people know, Mary's lines for the Shakespeare scenes are in the book she's holding on stage (they auctioned one of the prop books with the cheat lines to raise money for Broadway Cares at the performance I went to) but not the teacher's. And funnily enough, Urie left the show to star in the off-Broadway production of Shakespeare's Richard II. But Jackson really attributes the ease with which the words flow and the fun he has onstage to his co-stars, Krakowski and John-Andrew Morrison, who is currently playing Mary's Husband (Lincoln). He says that the show is "so beautifully written" and "dramaturgically solid" that even though he's heard it performed countless times, whether on stage or in rehearsals, he never gets tired of it.On December 8, on one of his days off, Jackson will be taking the stage at the legendary Carnegie Hall for a solo show, where he will be inviting his Oh, Mary! costar and Broadway veteran Jessica Vosk to make appearances. His performance is an expansion of a prior cabaret act he wrote and performed at 54 Below, where he invited Vosk to perform the Indigo Girls song "Ghost" with him. Her agent brought one of her good friends, who turned out to be a booker for Carnegie Hall. The booker asked if he'd be interested in building out the show. He quickly said yes.Previously, Jackson has done two guest shows at Carnegie Hall, but this is his first chance to do his own production (directed by Tony-winning director Warren Carlyle, to boot). The show, he says, is going to be autobiographical; the story is about him as a tall, queer kid from the red state of Idaho, and his journey from living in the woods with no electricity and an outhouse to Carnegie Hall. Attendees can expect him to sing songs from Xanadu, which he starred in on Broadway in 2007, as well as some pop hits from singers like Chappell Roan and a few other surprises. He and Vosk plan to reprise their duet and sing "Ghost," and Jackson will be performing "Somethin' Stupid" with Krakowski, which Nicole Kidman and Robbie Williams once sang together.In addition to his famous friends, Jackson's mother and his sister will be invited to join him on stage because they used to sing together when he was growing up. He felt it was fitting for them all to sing Porter Wagoner and Dolly Parton's "Oh, The Pain of Loving You" because, as he puts it, the family has had a rough time the last couple of years. A few years ago, he lost his dad, and politically speaking, the gay actor and his mom were on opposite sides of the aisle. "They definitely had to mourn their idea of what they thought my life was going to be, and I had the wherewithal to let them do that," Jackson explained. "We all kind of took a little sabbatical, then came back together." He added that they are healing their relationship, and one way to show that is to invite them to sing on one of the most iconic stages in New York City with him.Jackson will be onstage at the Lyceum Theater as Mary's Teacher through January 25, which means he gets a chance to play alongside Jinkx Monsoon when she returns to the titular role for a limited run in the new year. Jackson who is raising twins, Willow and Ethan, with his husband Jason Landau admits that leaving his kids for this production was difficult. But he wants to show them that chasing your dreams can be a reality: "I want them to see me doing stuff that scares me."