Cheyenne Jackson “Cares Deeply” About the Comedy of Oh, Mary!

Certain creative partnerships are magnetic enough to demand a reunion; no one knows this better than Cheyenne Jackson and Jane Krakowski. Currently onstage together in Cole Escola’s Tony-winning phenomenon Oh, Mary!, these two can trace their history as a duo back nearly two decades.

Jackson and Krakowski met in workshops for the 2007 Broadway production of Xanadu — “That’s where Jane and I fell in love,” he tells Ticketmaster — and later sparred onscreen as TGS castmates Danny and Jenna in the Emmy-winning 30 Rock.

Now, in addition to their ongoing run together as Mary and Mary’s Teacher in Oh, Mary!, they’ll be taking the stage at Carnegie Hall, where Krakowski is slated to join as a special guest for Jackson’s solo show debut at the iconic venue on December 8.

Below, Jackson reflects on reuniting with Jane Krakowski in Oh, Mary!, his Carnegie Hall debut, and which 30 Rock scenes he still thinks about.

Your history on stage with Jane is so rich — you can trace your partnership back to 2008’s Damn Yankees. Before that, there was also Xanadu — what was the overlap there?

So, she never did Xanadu on Broadway. She did the readings, workshops, and we created these roles together. I loved what she did in it. I mean, she’d done Starlight Express, so she was practically born in roller skates. And then she got the pilot for 30 Rock, and the pilot got picked up, and she couldn’t continue with the show. I did not want to do it without her, because we had such a bond, and we created these characters. I was like, “I can’t do this with someone else.” So I let Xanadu go.

James Carpinello broke his leg just a week before opening. I got a call and they said, “Would you like to come in and help us open it?” And I did. So we never got to actually do it on Broadway together, but that’s where Jane and I fell in love.

 

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This must be a really joyful, full-circle moment for you both.

We are just pinching ourselves because we have such a shorthand. We trust each other implicitly. You spend so much time together working on a TV show. We both also care really deeply about comedy. We care very deeply about the integrity of the jokes and the words. Tina Fey always used to say that comedy is serious business. So I always believe people in comedies don’t think they’re in comedies, right? They’re in drama. I’ve never been somebody who likes to do a funny voice for the sake of doing a funny voice. Stakes. Jane and I both believe in stakes and making everything so life or death, which is funny.

I think why Jane and I work so well together, especially in Oh, Mary!, is that 30 Rock really prepped us for it. Usually sitcom scripts are 35 pages. Some of those 30 Rock scripts were 50 pages. The table reads were intimidating because everybody was around, some people were Skyped in, and it was like a game of double dutch. You could not hesitate. You had to jump in. If you didn’t jump in with your line and get a laugh, it’s cut. That’s how I learned to make bold choices, be brave. Alec Baldwin also taught me so much with timing, and he’s just such a master at the dexterity of comedy. I could talk about 30 Rock all day.

Oh, well, I could, too. I’m trying to hold myself back. When did you first hear about Oh, Mary? Did you know right away that you’d be interested in being involved?

I’ve known Cole since they were 21, I think. I have loved them forever and ever.

I got asked to do La Cage [aux Folles] at the Pasadena Playhouse in Los Angeles, directed by Sam Pinkleton. I was in New York and Sam said, “You’ve got to come see a preview of Oh, Mary!” I wanted to see what Sam’s vibe was, and I could not believe what I had seen. I had never seen anything like it. I could not believe that this was on Broadway. I couldn’t believe that it was this funny, that the book was this strong.

So I said yes to doing La Cage, but I never thought of myself doing Oh, Mary! I just thought, that’s an amazing piece. I’m so happy for them. And then five months ago, Sam called me up and said, would you like to come do Oh, Mary! on Broadway? My life is in L.A., my husband, my nine-year-old [twins], our friends. To leave for three and a half months is not easy. I’m in this little apartment by myself. But the piece is that good.

This show absolutely found its audience. It’s extended far past any plans that were in place when it first arrived on Broadway. I think it captured something really singular. Do you feel that when you’re performing? How is it different from many of the other times you’ve been on stage? What different muscles are you flexing?

Well, what I love about this show is — and I can’t give too much away because there are lots of twists — but with my character, it’s very rare as an actor to get to play a part where you can show all of the crayons in your crayon box. All of your tricks, all of your comedy, all of your weirdness, all of your drama, all of your pain. It’s all in one character. I have not had this much fun on stage since Xanadu.

It’s that kind of joy, and the audiences for Oh, Mary!… I’ve never experienced anything like it. Xanadu was incredible, but we weren’t like a smash hit with lines out the door. We were a teeny little show. Oh, Mary! is packed every night. People are ready to party. They’re ready to have fun. When you feel that anticipation, it’s like horses being held back by reins. It’s kind of like the first time I saw Hamilton. Going in with the original cast, it’s hard not to be skeptical because you’re like, “How can it really live up to the hype?” And it did. It’s my job to commit to this text every single time, do the very best I can, stay with Jane on stage, be connected, and then take this audience on a ride.

It’s 80 minutes long, and being in a show that short is a dream. I remember in Xanadu, it was also around 85 minutes long. We were right next door to Les Mis, and I would get done with the show, and my buddy Max in Les Mis was just at the barricades.

Well, that’s a perfect transition, because I was thinking about you and Jane and I was wondering if you had any dream duos on Broadway that you haven’t done yet. I was thinking you two would make great Thénardiers in Les Mis. Do you have any that come to mind?

When I think of doing stuff with Jane, I want to do something like a Rock Hudson–Doris Day situation. We’ve been friends for so long. We’re both over 50, so we have the same sensibility. We have the same references, so I think it would have to be something retro.

She’s joining me at Carnegie Hall, and we’re doing this classic, really beautiful little whisper of a song called “Something Stupid,” which Nicole Kidman and Robbie Williams did a cover of several years ago. It’s just the vibe I see when I see Jane and myself…Doris Day and her big, gay bestie.

But it’s fun to play opposite her romantically too, because Jane is such a good actress. She’s right with you, and I love that, because not everybody’s like that. Some people have their way they want to say the line, no matter what you give them. That’s not being with each other. We are nothing without our scene partner. That’s my favorite thing about her: she’s malleable, and she is such a good listener.

 

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Does that come from just the trust that you guys have established over the years?

Yes, we definitely trust each other. The other day, she said, “I know that no matter what’s going on with me, I can look into your eyes and you have me.” I feel the same with her. And honestly, since becoming a father, I feel like I’m a much better actor, because I’m more present in life. Kids are who they are. They’re very in the moment, and I take that into every job. I’m like, “Just be your nine-year old self and imagine.” I truly believe that’s why I still love doing this job.

But having that trust and openness is so rare. Jobs like this just don’t come around very often. I’m going to miss it.

I’m very glad the timing worked out for you two. When you think about your time on 30 Rock, are there any particular days that come to mind when you think of performing with Jane and working on that show together? Are there any jokes that you still talk about?

I loved my stuff with Jane. I loved how Tina and the writers really set us up to be rivals. I always think of that scene where she wants to find out if I can sing, and I sing “Danny Boy” and her nose bleeds.

The thing that comes to mind is probably my very first scene that I shot, because I was so nervous. It was my first big TV role. Tina Fey had come to see us in Damn Yankees, and she came back afterwards and said “Hey, it’s nice to meet you. I like your big Midwestern face and your comic timing.” I said, “Thank you,” and then I got written onto the show. Luckily, the part was not too dissimilar from me — very wide-eyed, very positive.

My biggest memory is probably the very first scene where Danny has to meet the entire cast. The only people I knew were Jane and Tina. Everyone else I was meeting for the first time in the scene. I was terrified, and I didn’t know how to hit my mark without looking down. I was trying to gauge it right, and I was just so nervous.

In the scene, the 30 Rock doors open, and I come out. The whole cast is standing there waiting to meet the new guy, Danny. I overshot my mark by three inches. All of a sudden, I feel this big, hairy, meaty hand — Alec Baldwin’s — and he goes, “You’re in my light.”

What do you think Jenna and Danny would be up to now?

Jenna would probably have her own reality show. She’d be vying to be one of the Housewives; I see her wanting to be in front of the camera. Maybe Danny got a Marvel movie and is full of himself and comes back to TGS. I tell anybody that’ll listen — if Tina calls, I’ll be there.

Let’s talk about your solo debut at Carnegie Hall! After that, you have a nice run of shows into the new year. I read that you’re pulling from the Great American Songbook. What do you enjoy about performing from that era?

There are a few from the American Songbook, but this is really a built-out version of my own show that I wrote two years ago called Signs of Life, which I did at 54 Below. Somebody from Carnegie happened to be there. The show has a beginning, middle, and end. It has monologues. It has jokes. It has spoken word. It has a choir. I’m singing early snippets of songs from every show that I’ve ever done on Broadway, and I’ve never done that before. I’m singing from Xanadu. Jessica Vosk is joining me. I didn’t think I could find anyone who loves the Indigo Girls more than me, and I found it in her. We’re singing a song that I wrote about my dad. I’m singing the last song that Gavin Creel and I ever sang together.

Then there are some surprises. This is a dream come true; I’ve guested twice at Carnegie, but I’ve never done my own show. It’s so wild to me that this queer kid from Idaho, the reddest of red states, found his way out. I was poor — no running water, outhouse poor. And now I’m getting ready to do my own show on my night off from Oh, Mary! It’s crazy.

I grew up singing with my mom and my little sister, who is a second-grade teacher and the nicest person you’ll ever meet. They are joining me on the Carnegie Hall stage. I think that’s what I’m the most excited about. No matter what I do or where I go, you’re still the same little kid from where you’re from. My mom and my sister will come out, and we’ll sing.

I’d love to wrap up by asking what art has inspired you lately — is there a film, album, TV show, or book that comes to mind?

I just saw Guillermo del Toro’s Frankenstein. I was at the premiere. I have not been moved by a film like that in years. He came out and gave us a preamble and said he’s been wanting to make this movie since he was 10 years old, and you feel his passion for it. The movie is spectacular. He also doesn’t use AI — this is made for people, by people, and you feel it in every frame. The humanity and beauty in this movie…I didn’t feel like I breathed for three hours, and that was because of Jacob Elordi. Wherever that performance came from in his soul, he said he was just channeling and opening himself up. I think that’s why it’s so moving.

Cheyenne Jackson’s run in Oh, Mary! has been extended through January 25, 2026. Tickets for Oh, Mary! are available via Ticketmaster.