Kyle Dean Massey has graced the screen and stage in hits such as Pippin, Xanadu, Nashville, and The Good Wife, and is appearing in Barrington Stage Company’s summer production of The Pirates of Penzance. Massey’s current role as Frederic in this humorous and invigorating revival of Joseph Papp’s Broadway production tells the tale of a young man forced to be a pirate’s apprentice until he turns 21. The catch? He was born during a leap year on February 29, pushing back his plans to end his obligation with the pirates and be with his one true love, Mabel.
StageBuddy had the chance to chat with Massey about his robust career, how to endure waiting for true love, and his favorite pirate of all-time.
The Pirates of Penzance sounds like the perfect family show for this summer! What has been the most fun part for you so far?
Kyle Dean Massey: It’s really such a silly, zany show! Our director, John Rando, is so creative and has added so many funny bits to the show and has really updated it. We swordfight and there’s all sorts of little gags here and there, so it’s been so much fun and really is such a family-friendly show!
Do you meet tons of little kids excited to see pirates up-close?
We actually have some on-stage seating and there was a young boy on stage a few nights ago and he just lit up the whole show and it was so fun to see his face the entire performance!
The whole theater has actually been turned into a pirate ship. You’re really getting up close and personal when you are seeing this show!
Your character, Frederic, has to endure many obstacles as he longs to be with his one true love. What do you think helps get him through the waiting period as he deals with being born in leap year?
(Laughs) Well, I think what gets him through it is that he just meets the girl of his dreams. It’s a total Romeo and Juliet moment! He meets this girl and knows instantly that he’s the one for her but also knows that he has this duty. Ultimately, he wants to do everything he can to be a suitable partner for her but also struggles to be a good pirate as well.
This score is so comical and catchy! Is there a song that you can’t get out of your head?
I think from day to day, from performance to performance, I get a different one stuck in my head! They all are really catchy. A lot of audiences members come to the show thinking they don’t know this music, and then they hear it, and say, “Of course I know that one!” There’s a beautiful song in Act II that is sung by my leading lady, Mabel (Scarlett Strallen), which is such a haunting melody that she just sings so beautifully. That’s probably the one that gets stuck in my head the most.
The score is very old-school opera. Every song, the title of it, is basically the first five or six words.
Your career has spanned the screen and the stage. How has that contrast enriched your journey so far?
Both experiences have really made my career more full. The great thing about dabbling in everything is that you are always busy and always working on something new and exciting. My initial love was the stage and working in theater, and I did that solely for 10 years or so, and then I branched out and did other things – it’s kept it feeling new and fresh all the time and I’m always learning.
Do you have a dream role?
There’s a Stephen Sondheim show called Company that I really like and there’s a character of Bobby in it, so I think I’d really like to play that role.
What type of work do you hope to be involved with in the future?
My entire career on Broadway has been replacing other actors, which has been great because I’ve always been in a hit show (laughs)! Being part of a show like Pirates has been so exciting because you get to be a part of the creative process and work with the cast to build the show together which is really a cool experience. It’s really everything that you imagine in your head that you can bring to the table – and I’d love to be involved in work that allows for more of that.
I have to wrap up with a pirate question… name your favorite one of all-time!
Captain Hook, hands down! He’s the best silly villain.
The Pirates of Penzance runs through August 13th at Barrington Stage Company in Pittsfield, MA. For info and tickets, visit: https://barringtonstageco.org/
