Finian's Rainbow Star Cheyenne Jackson on 30 Rock, His New CD and Hanging Out in His Underwear

Cheyenne Jackson sports the first name and square jaw of an MGM cowboy riding into the sunset. And though Jackson grew up out West, his quick wit, urbane sense of humor and charmingly flirty manner betray a very New York sensibility. The talented actor is currently starring as romantic lead Woody Mahoney in the acclaimed Broadway revival of Finian’s Rainbow, which recently announced it will be closing on January 17. Despite this sad news, Jackson has plenty on his plate, including a new CD with Grammy winner Michael Feinstein and a stint on TV’s 30 Rock. Broadway.com caught up with the matinee idol who chatted about the year that was and the one that will be: “I want to sleep more in 2010. I didn’t sleep a whole lot in 2009!”

What were you up to over the holidays?
Well, my partner [Monte Lapka] was in Brainerd, Minnesota, where he’s from. We usually go there for the holidays, but because of the Finian’s Rainbow show schedule, I stayed in New York. That's tough because I don’t think we’ve ever spent a Christmas apart in our almost 10 years [together]. But, you know, it’s actually kind of fun to hang out all day in my underwear in my apartment and watch what I want—although the apartment started to look a little like Grey Gardens. Monte’s tidier than I am. I did have my big dog Zora—you’ve seen her in the videos; she’s huge. But that’s the holidays for me: just chilling, relaxing and resting.

What about New Year’s Eve?
Very low-key. I’m too old to do that party-hopping thing where you end up in random people’s houses and then you can’t find the person you came with, so you just kiss whoever’s standing there in the kitchen with you.

Last year you were named Entertainer of the Year for 2008 by Out Magazine. How did 2009 stack up?
I told Aaron Hickland, the editor of Out, “How in the world am I going to be able to top that?” All I wanted to do was more of the same and work a lot, and that’s what I ended up doing. I always wanted to be on a great TV show and in a Broadway show and have a CD out, and the fact that they happened simultaneously is kind of an embarrassment of riches. I didn’t plan it to happen, but I’m just going with it.

I hope your CD, The Power of Two with Michael Feinstein, got played a lot over the holidays. It’s great party music.
I’ve heard that a lot at the stage door. People are saying, “We’ve been playing it over and over. We have it on a loop.” Then somebody said, “Oh, we have it on our office for our hold music, so you should call our office and ask to be put hold!” I was like, “Well, I’ll just get right on that.”

That’s some swank hold music! Tell me about making it.
It is very swank! You know, I’m no dum-dum. If I was going to do this, I wanted to do it with somebody who knows what they’re doing. Look at Michael Feinstein: I think he’s been nominated for five or six Grammys; he’s such an amazing person. Aside from his incredible talent and his pedigree and all that, he’s just really fun and smart and irreverent, and those are all things that I respond to.

How did you become friends?
We’d known each other and each other’s work for a while, but we weren’t really “friend” friends until we both were booked on the CBS Christmas tree lighting last year. Usually those kinds of events can be weird because you’re nervous that you’re under-rehearsed, so everybody’s in their own little world. Anyway, the Christmas tree didn’t light when they did the countdown, it was a big funny snafu, and while we were waiting for that to happen, Michael and I were hanging in the warming tent. We just started chatting and realized we had a lot in common. We really cracked each other up.

I thought you said in your act that you met at a party?
He did invite me to a dinner party. He always has such a motley crew of guests, everybody from old Hollywood movie stars to entertainment lawyers—it’s a really fun eclectic mix—and I was a little nervous. So I was talking a little too fast and a little too loudly and I leaned back and I broke the chair I was in, which it turns out was a French 18th-century chair.

Oops! How did he react?
Michael just laughed, and I just knew from then on we were going to be buds. After that, we started talking about doing an act. We put it together pretty quickly. We rehearsed it all at his house. I would bring songs; he would bring songs. Many of the songs we both thought of, so we knew those were no-brainers.

You are fabulous on 30 Rock. Tell me how your appearance on the show came about. Was it because of [30 Rock star] Jane Krakowski?
Yes, but not directly. But my association with Jane brought me to the attention of [30 Rock creator/producer/star Tina Fey]. I don’t think Jane called and said, “You gotta get Cheyenne!” but Jane and I had done the Xanadu workshop together and we’d done Damn Yankees at Encores! Tina had seen both of those things, but I think it was at Damn Yankees that she really noticed me. She said she liked my “big old-fashioned face.” I’ll take it, Tina Fey!

Yes, that’s a compliment worth taking.
The fact that I was even in Tina’s consciousness at all was baffling and exciting on every level. When they called and told me a little about the character, they said, “We just want to gauge your interest on this.” And I screamed, “My interest is high!” I still had to audition and jump through the hoops and all the bigwigs at NBC had to sign off on me. It’s my feeling that they probably wanted somebody more famous because it’s a great juicy part with a lot of episodes, but I think Tina really gets me. I’m just trying to not be too awestruck when I’m on set.

How many episodes will you be doing?
I don’t know. We’re coming up on five so far. They said I’m going to be popping up throughout the year.

I thought you were supposed to be on Glee. What happened with that?
I got sick. I was all set [to do it]. I had a great audition, and I flew out. As I got off the plane, I started to feel really fluish and feverish, and I thought, “Nah, I’m fine” because I’m just a big ox and I never get sick. Then as they were driving me on the little golf cart on the Glee lot to the costume fitting, I was so shaky and cold and I thought, “Aw, this is not good” and by the time I got to my costume fitting, it was all downhill.

That’s awful. Do you think you’ll ever be on?
I hope so! Everything works out like it should. It was so unbelievably sad and painful at the time, I couldn’t even watch the episode. It was too painful. And I was stuck in L.A. for two days until my flight went back, so I was just lying in my bed going, “WHHHHY!” The guy they replaced me with was really funny. I’ve since seen it, and I thought it was great.

Let’s talk about your big old-fashioned face and your big old-fashioned musical. It’s fun to watch the Finian’s Rainbow backstage goings-on in your Broadway.com video blog.
It’s been really fun. The show is so old-fashioned—it’s one of the things I love about it, and the video blog is great because I really want people to connect with what we do backstage. I love it.

One of the funny things about old-fashioned musicals is how quickly the characters fall in love.
Kate [Baldwin] and I would joke about that in rehearsals. My journey is I meet the girl and about three sentences later we’re madly in love and about four sentences later, we’re getting married. There isn’t a real sense of conflict in terms of our arc and our relationship, so it was really up to us to mine the piece and find something to make these characters live because there has to be more to it than that or people will check out. You have to just trust it. When I say lines like, “A secret, a secret, a secret kind of secret”, you have to find a way to make that real for you and live for you.

Finian’s Rainbow is a very different show compared to Xanadu, your last Broadway project. Do you miss that campiness at all?
I don’t. I mean I loved it, and but it’s nice to sometimes say what you mean and mean what you say and not have there be any kind of underlying winking or commenting. I purposely try to do something different from the time before just to stretch myself because everybody has their own expectations of what they want to see you do. I made a conscious decision after All Shook Up to stay far, far away from anything Elvis. No Bye Bye Birdie, no anything like that. After this, I’ll have to stay away from anything resembling Howard Keel.

Speaking of old-school stars, I love that you said that you wanted to play Rock Hudson. Did you read a book about him?
No, I think I saw a biography of him or something. The Rock Hudson thing all happened because somebody asked me who I’d like to play, and off the top of my head, I mentioned him. Then it’s become this thing where everybody’s like, “Oh, you’re going to play him in a movie!” There’s no movie, though. I just relate to him and his story. There’s a sadness and great pathos there. I’d love to explore that. It was a different time.

Anybody else you’d want to play?
Mickey Rooney! [Laughs].

Do you have any resolutions for 2010?
All the usuals: Stop biting my nails. Watch less reality television and read more and all the things that I try to curb and do throughout the year. Monte and I do this funny thing: for every half hour I watch a bad television show, I have to either read a really boring book that I wouldn’t normally read or I have to watch National Geographic or Nova or something to counteract the garbage.

You have a lot of devoted fans. Are you ever surprised by the reactions you get from people?
Sometimes. It’s taken me a while to understand why people respond the way they do to me. Sometimes it’s strange. I have these great fans who call themselves “Cheyenne-tologists.” They’re so sweet and they’ve supported me for a long time. They always wear shirts with my face on them. At first I was like “AAH!” But it’s totally lovely and it’s all done with respect. It’s a lovely thing to feel supported.

I assume you’re going to see All About Me, Michael Feinstein’s show with Dame Edna.
Oh, definitely. It’s going to be very, very fun. I’ve met [Barry Humphries, who plays Dame Edna] before. He’s so funny and sweet.

If Barry Humphries is sick, will you offer to step in?
Absolutely.

With the whole extravagant look?
Yes. We would look about the same, actually. We’re about the same height and same build, I don’t know if I can pull off the purple hair, but you never know.