With roles in a slate of iconic Broadway and Off-Broadway shows, Kyle Dean Massey has already charmed musical theatre audiences by the thousands. But he's recently jumped to greater fame as the love interest of a gay country singer on the hit TV show Nashville. The actor-singer's own Southern roots are near the country music mecca.
Massey will make his Feinstein's debut October 2 and 3, with a show full of favorite songs, but possibly not the ones you'd guess, given his repertoire. Massey will perform Things that Weren't , a collection of songs he hasn't performed in the numerous shows in which he's starred.
Whether he'll perform iconic songs from Wicked or Pippin, you'll have to attend his cabaret show to find out. Although the characters he's played in those two shows are at first a bit shallow, Massey himself is sincere, appreciative of his success, and devoted to several causes offstage.
When we spoke, Massey had flown back from Amsterdam, where he performed excerpts from Pippin with castmates at Uitmarkt, a televised Dutch outdoor concert series. Shortly after his nearly one-year run in the show, Massey said he found a better appreciation for it when he took on the role, compared to having seen it as a teenager.
"I don't know if it was just growing up and having life experience behind me, or if it was this revival production that connected to me in a different way," Massey said. "It was probably both. I got to see the show before I was in it, and I was thrilled to do it."
To prepare for the role, Massey underwent five weeks of circus training. "I learned to do a backflip, stand on another performer's shoulders, climb up a pole, and even knife throwing." The action-packed revival was more demanding for Massey than previous roles. "Usually, when you replace another actor in a Broadway show, you get two weeks of rehearsal, so five weeks was a lot."
The notably fit 33-year-old actor trimmed down his gym training during the run of Pippin in the title role, which costarred John Rubinstein, who starred in the show's original cast. Rubinstein played the elder Charlemagne in the recent Broadway revival.
Show Kid
Massey's show business dreams started young, when at age six, he followed his sister to ballet classes after seeing her in a production of The Nutcracker in his home town of Jonesboro, Arkansas. Along with dance classes, he studied piano and sang in choirs, even performed in a makeshift yet popular Lunchroom Dinner Theatre at his school. As a youngster, Massey saw The Will Rogers Follies national tour in Memphis' Orpheum Theatre, his first touring Broadway show.
But he didn't perform in musicals until later in high school, where he was also a jock. "I was always a swimmer, it was one thing I always did," said Massey, who was a nationally-ranked competitive swimmer. "But I had this love for performing. I did puppet shows and magic shows, put on plays a lot as a kid."
While attending a private Catholic prep school, he enjoyed the arts, but later, at a larger public high school, "I got made fun of for taking dance classes," said Massey, who realized that he was gay. "Boys would call me a girl, 'ballerina.' It was not exactly supportive. That's when I quit. There were hundreds of kids, and I needed to fit in."
Fortunately, Massey returned to performing. "I got back into it in tenth grade," he said. "The theatre choir at my high school was a cool thing to do. It wasn't an outcast thing to do. That's when I did my first musical."
Despite his talent, getting into a performing arts college program wasn't easy. But even before he graduated from Missouri State, he built up his resume with summer stock, sometimes performing ten shows a week, including in the role of Danny Zuko in Grease, where he made a whopping $90 a week.
"I took a semester off after my sophomore year and moved to New York City," said Massey. "During my senior year, there was a group audition for several theatre companies at once; cruise ships, national theatres, summer stock. I went to that and had interest from the 42nd Street touring company, and ended up booking that show."
His new job as Billy Lawlor started three days after college graduation. "We rehearsed in New York, and then went right on to touring in the U.S. and Japan."
Wicked Good
In 2007, after a year long run in the Off-Broadway production of Altar Boyz, Massey was cast in the first National Tour of Wicked. He eventually left that tour to make his Broadway debut playing Thalia in Xanadu (the tongue-in-cheek musical comedy loosely based on the cult film that starred Olivia Newton-John and Gene Kelly). After Xanadu, he joined the Broadway company of Wicked only to leave once again from 2009-2011 to play the role of Gabe in the Tony and Pulitzer Prize-winning family drama Next to Normal.
He then originated the role of Billy Ray Jackson, a rising Country Western singer, in the short-lived Lucky Guy, which included notable costars Leslie Jordan and drag star Varla Jean Merman. Kyle Dean again returned to Wicked, now graduated to the role of Fiyero, the romantic interest of the green witch Elphaba. He has gone on to play Fiyero both on Broadway and Los Angeles on several different occasions throughout the years and as recently as last year.
"Every time I go back to the Gershwin Theatre (where Wicked continues to run), it feels like I'm going home," Massey said of the unique family atmosphere of the hit show, which is adapted from the Gregory Maguire novel. "It's great to see everyone, from the crew to the cast and the musicians. Many people have been there for more than a decade. So you've seen their kids grow up. You've been a part of these people's lives. And that is a really rare and special thing in this business. Most shows cannot offer that kind of history."
Massey also credits Stephen Schwartz, who composed the score for Pippin and Wicked . "Stephen can write a melody for sure. He's so smart and great. I owe him a lot."
Asked about the similarity between the roles of Fiyero and Pippin �"young men who start off naïve and self-absorbed, but who learn to find empathy for others�" Massey said, "I think that's just a common trait in characters in musical theatre. You want to play someone who starts the show in one light and learns something and changes. Those are the kinds of roles that people play; I wouldn't say its typecasting. They're both kind of spoiled little boys who grow up."
Another highlight was playing Tony in a 2013 St. Louis, Missouri production of West Side Story (which he also played in college). His grandfather took him to shows as a child to the outdoor theatre.
Country Boy
And although it's a supporting role, Massey's fame got a boost on the ABC show Nashville's third season, as Kevin Bicks, an out gay composer paired to write songs with the then-closeted Wil Lexington, who is played by former Bruce Weber model Chris Carmack.
At last season's finale episode, Lexington had awkwardly romanced Bicks, then came out as gay in a press conference, where he was expected to deny the rumors fueled by tabloid photos of the pair caught hugging at a private home. The two characters became intimate while Lexington struggled with both public and private honesty about being gay.
Lexington's coming out leaves fans of the two gay characters wondering how much more we'll get to see as the two handsome men develop their relationship.
Carmack's role sort of matches the real life coming out of two country musicians Ty Herndon and Billy Gilman in 2014. Massey is one of a few other musical theatre stars in the Nashville cast. Laura Benanti and Will Chase are also Broadway leading actor-singers.
Understandably, Massey could not reveal any plot points, but the fact that he was filming for the fifth episode is a good sign that his character's relationship with Lexington will continue. "If you watch the show, you know things happen quickly," said Massey. Nashville's Season 4 premieres September 23, 10pm on ABC.
Despite playing a songwriter, he did reveal that he won't be belting out any songs just yet. "Part of me is enjoying the break from singing," he said. "When you sing eight shows a week for years, you cherish the moments to just act."
Asked about the significance of playing an openly gay character, Massey said it is important, yet sometimes confusing to see responses.
"People like to put labels on me, like I'm an activist for being out. I think for people who want to have any sort of peace in their lives, the best thing you can do is let people know you're gay. Letting people know you have a happy and healthy life is the best thing you can do for people who are struggling, especially with family issues, and like me, especially being from the South. I got so many tweets from people who say what a big deal it is. The Southern demographic watches Nashville. It makes me feel good that people can be more accepted. It is changing their minds about gay people."
Benefits and Beefcake
It should be said that Massey never exactly 'came out,' as much as it wasn't an issue by the time he came to notoriety for his performances. He was one of the first Broadway actors to make an 'It Gets Better' video.
"It was never a big issue for me," said Massey. "My coming out was around the time I was doing Next to Normal. It was the first time people had any interest in me. I didn't want to lie or skirt on the issue, but it was very much a non-issue." Massey has a boyfriend, but that's one part of his life he prefers to keep private.
Now, he's one of Broadway's most successful out gay actors, and performs at benefits and celebrity showcases, including performing in an all-male modern gay version of the song "A Weekend in the Country" from A Little Night Music for Broadway Backwards (where gender roles are reversed).
One highlight was the benefit concert for marriage equality with the cast of Next to Normal. "It was fun, and I got to sing with my friends," said Massey. "It was just thrown together the day of the show, but for some reason, that concert has lived on in people's memories. People still come up to me and remember it."
Another unusual benefit was a concert called "The Yellow Brick Road Not Taken," comprised of all the songs cut from the original workshop version of Wicked. Timed with the show's fifth anniversary, "We did a big benefit for Broadway Cares, an entire one-act show with songs, with different celebrities playing the roles. It was very different."
Massey pauses. "It was kind of...not good." He laughed.
"I think they thought it was going to be a great night, but then we remembered, there's a reason those songs got cut. But we had a great time and drank a lot backstage."
Massey assured me that composer Schwartz approved of the event. "There are some really great songs, but that's what so great about him. Other composers get stuck, but if it doesn't tell the story, he's not afraid to cut it."
Lucky New Yorkers who can get tickets to the sexy Broadway Bares benefits enjoyed Massey in 2012's Edition XXII as the lovelorn protagonist looking for a happy ever after through a series of sexy dance numbers (very loosely) based on classic fairy tales. And, (spoiler alert) his character did find his happy ending, with a wedding to a prince, actor John Carroll. That edition of the fundraiser brought in $1,254,000, a record for Broadway Cares/Equity Fights AIDS.
When he's not performing, Massey also teaches theatre master classes, and has worked with Camp Broadway, Broadway Artists Alliance, Broadway Connection, The Offstage Group, VIP Tours of New York, The Missouri Fine Arts Academy and Arkansas State University. He also foster-cares the occasional shelter puppy in his New York apartment.
Asked about the difference between performing in TV and theatre, most of which are obvious, I mention the recent notorious �"and deserved�" anger from actress Patti LuPone when an audience member was taking photos with a cell phone in the middle of her show.
"I don't wear my glasses onstage, so I don't see anything anyway," said Massey. "The only time it bothers me is in a small intimate setting when it is actually distracting. But it does bring up my thoughts on the nature of art in general. What we do is theatre; it's a fleeting art form. It's not going to hang on a wall forever like a Van Gogh painting. It happens live with a new audience every night. It's an 'in-the-moment' art form. We perform it that way and it's meant to be enjoyed that way. So it does bother me that people feel they have to record it. They're missing the essence of makes theatre what it is...an ephemeral and sometimes magical moment in time."
Kyle Dean Massey performs 'Things That Weren't' at Feinstein's at the Nikko. $35-$50 ($20 food/drink min.) Oct. 2, 8pm. Oct. 3, 7pm. Hotel Nikko, 222 Mason St. (866) 663-1063.