The Hottest Guy on Broadway: Pippin's Kyle Dean Massey


By Michael Musto

Plus: A beef-beating musical even vegans will love

Photography by Joan Marcus

The rather comely Kyle Dean Massey has stepped into the wandering shoes of Pippin in the smash Broadway revival of that show about a medieval prince who’s tracking down all sorts of worldly adventures en route to discovering the real joys in life. Still in place in the swirling, circus-like Diane Paulus production are the sensational performances by Terrence Mann, Charlotte d’Amboise, and Rachel Bay Jones, all playing varying loved ones who populate Pippin’s extraordinary existence. Enjoyably joining them are newbies Ciara Renee (a taunting fembot as the Leading Player) and Annie Potts (adorable as the high-spinning granny who spouts wisdoms as she rotates). And Arkansas-born Massey, 32, fits in beautifully as a sweet-voiced hero capable of balladeering, acrobatics, and, thankfully, taking his shirt off, culminating on an aerial swing dangling over flames as you gasp at the guy’s range.

Having done replacement parts in Wicked and Next To Normal, the openly gay Massey is a seasoned pro at stepping into juicy rules and making them Massey-like. But this is his biggest opportunity yet, and it provided the perfect chance to sit the guy down and talk at length about his craft. Oh, did I mention he’s extremely attractive? 

Musto: Hello, Kyle. You’ve replaced people before, so you know how to slide into a show, right?

Kyle Dean Massey: This was a little different because you have to learn all the circus stuff, which was a different challenge. 

I noticed you bravely climbing a pole at one point. 

I had several weeks of circus training. We have circus training before all the shows. We practice, rehearse, and work on everything. It’s continuous.

And the swinging over the flames bit?

That was not too bad. They took me up in increments. I have to do a backflip at one point. That and throwing knives were the hardest skills I can learn. They had to teach me to do a somersault, so a backflip is a huge deal.

Beyond all the athletics, what do you think is the message of Pippin? Learning to appreciate life’s simple joys?

No, I actually don’t think that’s it. I think it’s more about finding happiness outside of yourself. Pippin is a character who’s so concerned with his own fulfillment through the entire show. It’s not until he starts caring about someone else that he finds any glimmer of happiness. The message is to find your own happiness by making your own decisions, not from being pushed into anything. Judging your happiness on yourself rather than what anyone else is doing.

The show is very ‘70s, but quite relevant, no?

It deals a lot with universal issues—with someone trying to find their own happiness, which never goes out of date. The music holds up as young and current for Broadway music. The score is very accessible.

Had you ever seen Pippin before?

They did a video recording of the original production that they taped for TV. I grew up watching that. Then I saw this production last summer, when I had a small break in Wicked. I was blown away with this production—the way they’ve reimagined it was smart, and for me it made the show make sense. Before, I was like, “I like the music, but what is that show? I don’t get it.”

I loved when the hunky actor pinched your ass after the orgy scene.

They cut that out of the high school production. [laughs] I don’t think it’s in the script. They’ve definitely added a whole bunch of little things to this.

Is your brother character an LGBT villain?

No, he’s not. He’s supposed to be a war-hungry doofus.

But you have a line where you say you’re surprised he’s into women.

It’s just a dig. Like, “I’m surprised you’re into anything other than war.”

Aha! As for your own trajectory, are you happy with your career?

I don’t have very high expectations for myself. The fact that I get to work on Broadway and have been for many years is more than I ever dreamed. I’m happy with the roles I’ve been given and I’ve been fortunate to be in those hit shows. I’ve done only one flop.

I assume you mean the 2011 Off-Broadway musical Lucky Guy. Why do you think it imploded so badly? [The Nashville-themed show starring drag queen Varla Jean Merman reportedly lost between two and three million bucks.]

I think it was a little confused about what it wanted to be. It had a specific audience and that wasn’t enough to keep the show open. That project had been tinkered with for 30 years. It had gotten to the point where everything was a little too precious. They worked really hard to get some kind of show that was going to sell, and at the end it caved in.

Getting to the important stuff: Are you one of those people who know you’re good looking or do you pretend you’re not?

Number two. I feel very self conscious. 

What? But you must realize from people’s reactions to you that you’re not exactly bad looking.

I don’t think I’m bad looking, but I certainly don’t think I’m the best looking.

Do you look for flaws?

I don’t look for them, I just see them.

Sounds like some heavy therapy is in order.

Probably, among other things. [laughs]

Do you have a boyfriend?

I do. Not in New York, in L.A. We’re both back and forth quite a bit. Right at this second, it’s long distance, but we don’t do long distance much.

Do you get involved in politics or causes?

I’ve done lots of things. I was one of the first people that did one of those “It Gets Better” videos. I was included in the book. And I’ve done things with Trevor Project and Broadway Cares/Equity Fights AIDS. Recently, I was in a benefit called Broadway Backwards, where guys sing the girl parts and vice versa. That evening, they turned all the songs into gay songs. They reimagined songs from Broadway shows to tailor them for a gay audience and bring a new meaning to them. I sang Tuptim’s part in “I Have Dreamed” from The King and I

More range! Congratulations on yet another high wire act.