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taking flight
by Audrey Poff; photography by Melissa Donner

Since April, Kyle Dean Massey has entertained audiences on Broadway in the title role of the Tony Award-winning revival of “Pippin.” This month, the Jonesboro na tive heads to Los Angeles to join the first national tour of “Pippin” in the title role of the high-flying hit musical.

Massey, who made his Broadway debut in 2008, grew up in Jonesboro with his three sisters – Katy, Kimberly and Kirby. His parents, Dean and Janice Massey,
and one sister, Kirby Smith, still reside in Jonesboro. His sister, Dr. Katy Wagner, has a dental practice in Jonesboro but lives in Manila, and Kimberly (Huelsing) resides in the St. Louis area.

In October, Massey returned to Jonesboro to perform during A Night of Stars Under the Stars. A benefit for The Children’s Shelter, the event also featured The Broadway Tenors including Jonesboro native Matt Cavenaugh.

Unfortunately, the demands of being in a Broadway show prevent Massey from being able to come home often.

“We do eight performances a week, which is every day but Monday, so you can really only go as far as you can go in 24 hours,” said Massey. “Believe me I’ve made several trips to Arkansas in 24 hours but it’s tough and it’s really tiring. If you’re doing a really difficult show, like the show I’m doing right now, ‘Pippin,’ it’s kind of impossible. You just can’t do it. That is definitely a major drawback but luckily my family comes up here quite a bit so I do get to see them and periodically, I make it home.”

Massey, who turns 33 this month, has fond memories of growing up in Jonesboro. In addition to studying dance, music and theater, he also swam competitively throughout his youth.

“As much as I loved doing all of my dance recitals and piano recitals and things like that, really my adolescence was about swimming. My sisters and I were really involved with the swim team, the Jonesboro Jets. I think I was on the swim team at four or five years old and I swam all the way through high school . . . before we were even called the Jonesboro Jets.” Massey and his sisters also
swam for the JHS team and for Team Arkansas, competing across the country at swim meets.

Massey’s first taste of the performing arts also came at an early age in one of Jonesboro’s longtime holiday traditions, “The Nutcracker Ballet.”

“My first experience with the performing arts was with Edgar Hall, who had a ballet studio in Jonesboro,” said Massey. “He put on a production of ‘The Nutcracker’ every year and my older sister was a soldier. I went with my family to see it and I was completely enamored.” After seeing the show, Massey said he managed to talk his parents into enrolling him in ballet.

“I don’t know if it was through begging or my parents realizing how into it I was, but I was enrolled in ballet class . . . and a tap class,” he said. “The next year I was in ‘The Nutcracker,’ and I was in dance recitals and things like that. So that was really my first experience – performing at The Forum in ‘The Nutcracker’ in 1988 with Edgar Hall’s ballet studio.”

In addition to Hall, there were many others who helped train Massey while he was growing up in Jonesboro. Sister Celestine Pond, his music teacher at Blessed Sacrament, was one of the first to recognize his musical ability; Christie McNeill became his tap dance instructor as he got older; Fonda Lofton served as his choral teacher at Annie Camp Jr. High and Jonesboro High School; Harriet
O’Neal was his piano teacher; and Dr. Julia Lansford was his voice teacher. Keith Salter was instrumental as his first drama teacher at JHS, he said, as were others including Robin Yates and a number of instructors, directors and choreographers with whom he worked.

Massey performed in his first musical, “Shenandoah,” at Jonesboro High School. “I think I was 16, and I had a speaking role which was a big deal for an underclassman . . . ,” he said. The productions at JHS helped expose Massey to different aspects of theater.

“I think I always knew I wanted to have some kind of performing career but it really wasn’t until high school that I even really knew what musical theater was,” he said. “We did a production of ‘Guys and Dolls’ my junior year of high school, and I think pretty much after that I was dead set” on musical theater.
Massey said his parents were always supportive of his career choice.

“They tried to steer me in the direction of what I was going to love and what they thought would make me happy,” he said. “They realized it was some kind of performing arts and so they totally encouraged me. They are terrific.”

After graduating from JHS in 2000, Massey attended Missouri State University in Springfield, where he continued to hone his skills during the school year and launched his career as an actor during summer gigs.

Describe your first paying job in theater before and after college. My first paying job ever was doing summer stock theater while in college when I was 19. I worked at a little summer stock called The Timberlake Playhouse in northern Illinois. I think I made like $90 a week and I lived in a shack that was infested with mice and had bats that would always fly over us at night. It was pretty rough, but I felt that I had arrived because I had never been paid to perform before. That was definitely a first step so I was elated to be there. My first paying job after college was the international tour of “42nd Street.” I started a few days after I graduated.

What’s the worst job you’ve had betwen leaving Jonesboro and making it on Broadway? I’ve got to say that I’ve been really fortunate. In my worst job, I had to give away free comedy show tickets in New York City. This was 12 years ago. I had to get people’s names, address, phone number and email address. It was so awful. It’s so invasive – just trolling around the city trying to unload those free tickets.

When and how did you first land in New York City? I had done summer stock for a second summer when I was 20 and that second year was quite a step up from my first year. I was part of the intern company and all the other interns had just graduated from college and they were all moving to the city. My next semester was going to be a really light semester . . . so I took a semester off and went to New York and I just auditioned every day for everything just to get an idea of what it was like to live in New York and to audition in New York . . . . I was offered a position right before I came to New York to work at a dinner theatre in Phoenix, Arizona, starting in November. So I was just going to move to New York for like three months and then go do this gig in Phoenix and then go back to school and so that’s exactly what I did. When I went back to school I was able to work on things that I knew I needed to work on and I had also forged some relationships with casting directors in the city . . . that really
helped me secure employment as soon as I graduated.

To date, what has ben your longest run on Broadway? I’m not sure. Cumulatively, over the last eight years I’ve done over 2,000 performances of “Wicked.” I’ve been really fortunate to show hop – to kind of go from one show to the other show with little to no break between them. I’ve been working on
Broadway since I had my Broadway debut in 2008.

How grueling is it to perform in eight shows a week, especially for a very physical role like “Pippin?” It varies from show to show but it is grueling. As I’ve gotten a little older, I’ve found it to be more difficult on my body. The repetitive motion is difficult . . . but “Pippin” is really rough on my body. The whole conceit of the show is that it’s my first time playing the role of Pippin in “Pippin” – it’s kind of a show within a show. My character is supposed to be a little clueless so I get pushed and shoved and told what to do a lot within the show and that hurts. There’s a lot of flipping and falling and climbing and things like that. I go to physical therapy twice a week to help me out with that.

How do you know when it’s time to move on to the next role? Do you eventually get bored with a role? Yes, you absolutely get bored with roles from time to time. You go through ups and downs with all your roles because it is very repetitive. It’s funny. We get into this business because you’re a creative person and you want to create something and when it comes down to it, being in a Broadway show is probably closer to being a factory worker on an assembly line than being an artist . . . because it is a repetitive thing and you kind of become a cog in a whole machine. Luckily for me, I have contracts so I negotiate a contract length before I even start a role. When I come to the end of that contract, I’m usually done. Sometimes they’ll extend you or they’ll ask you to stay a little bit longer. Sometimes I do and sometimes I don’t – it varies from show to show. There are some shows where physically and emotionally you just can’t do it anymore. That’s when you know it’s time to go.

You also enjoy teaching in your spare time . What opportunities have you had to work with students? I teach a lot. I teach via Skype. I teach via YouTube videos. I do private coaching in New York City. I work with a variety of companies and I do master classes at universities. I really, really enjoy it. This morning I did a Skype Q&A with a Theater 101 class at Missouri State
University, my alma mater, that I do every year with them.

What’s the biggest sacrifice you’ve made to make it on Broadway? Definitely being away from your family is the hardest part. It’s a business where you have to be present in New York City to do it and so that’s hard. You miss every holiday. This year alone I have a show on Christmas Eve, Christmas Day, New Year’s Eve, New Year’s Day. Every major holiday . . . I always have a show. At this point, I’m kind of used to it but you always get a little sad that you can’t be with your family on special days.

What advice would you give to Jonesboro students who desire to follow in your footsteps? Training is very important. I teach a lot with kids and a lot of kids have this . . . almost like a reality show mentality where they think that making it is like an overnight possibility and it really isn’t. That happens for a few people but 99.9 percent of the time it’s a very slow, gradual process that requires a lot of training and work. Don’t be afraid to get your hands dirty. Don’t be afraid to go work summer stock for $90 a week because if you love it, that will get you through . . . because you will think it’s fabulous like I did. Work hard. That’s my best advice.

Were you able to take any time off before joining the national tour? No. My last show is on a Wednesday evening, my flight to LA is on a Thursday morning and I’m at the theater Thursday night training with the new acrobats, so no time off.

Editor’s note: For more information about the Pippin U.S. Tour and a complete list of show dates, visit pippinthemusical.com/tour.