It's good to be bad, especially if you are Robert Cuccioli. Though he's known for portraying some of the most sinister characters in the musical-theater canon, he is also revered for bringing heart to the bad guys we love to loathe. The Drama Desk Award-winning star of Jekyll & Hyde, Les Misérables, and Spider-Man Turn Off the Dark is taking on another rapscallion in Adam Overett's My Life Is a Musical at Bay Street Theatre. The new show focuses on Parker (Howie Michael Smith), a man who vehemently hates musicals, yet leaves his apartment only to hear people singing and see people dancing — while no one else knows it is happening. Cuccioli plays Parker's nemesis, Randy, a famous music blogger whom he describes as being a "throwback to the forties and old spy novels, with a big element of Inspector Clouseau and Dick Tracy." Cuccioli chatted with TheaterMania about his decision to transition from a career in finance to one in theater, the allure of being a villain, and the musical that most encapsulates his own life.

Howie Michael Smith Robert Cuccioli in Adam Overett's My Life Is a Musical at Bay Street Theatre.
Howie Michael Smith (bottom) as Parker and Robert Cuccioli as Randy in Adam Overett's My Life Is a Musical at Bay Street Theatre.
(© Lenny Stucker)

1. What appeals to you most about taking on characters with a dark side?

I find them the most interesting, honestly. They're the most complex and complicated. It's fun to find some charm to them also. The "bad guys" that I end up doing are never black and white. There's so many different shades to them and that's what makes them more interesting to play and to discover.

2. Would the people close to you say that you have a darker or lighter personality?

I think I'm very much both. I have a very light nature to me. I love to laugh and do comedy. That's one of the things that drew me to My Life Is a Musical and to the role of Randy. He's dark but funny. I also have a more thoughtful nature to me, but I think I'm pretty balanced as far as that goes.

3. Randy is very different from previous antagonist roles you've played. How do you describe him?

He is a wannabe detective, a music blogger…a force to be reckoned with, but he takes himself extremely seriously. The situations he finds himself in are hilarious. I'm having a blast doing the show. It's very charming, the music is great. It's a rarity to be able to count on one hand the amount of people that are a triple threat that can write the book, music, and lyrics for a show, and do them all really well. Adam Overett did a marvelous job with the whole thing.

4. You originally aspired to be a corporate lawyer, so you went to school for finance. How did you find yourself involved with musical theater?

I did theater all through my younger years and I was in a band, but I never considered it a career. I was always on the path to work in business. In my senior year of college at St. John's University I did two shows and people said, "You're really good — did you ever think of doing this as a career?" A light bulb went off, and I decided to investigate. I didn't want to wonder What if? all my life. Meanwhile, I had bought the sheepskin so I decided to use it. I got a job at E.F. Hutton, a major financial brokerage house on Wall Street, and I worked with them for three years while I pursued acting. I did auditions during my lunch hour. I got a job in the chorus for the Light Opera of Manhattan at night, and worked on Wall Street during the day. After a year and a half of doing both I couldn't do it anymore. I quit Wall Street and I pursued theater full time. I waited tables…and my parents cried. [laughs]

5. Out of all of the musicals you've done, which do you feel the closest to and why?

I have done so many. One of the musicals that I'm really close to is Man of La Mancha. I'm drawn very much to the age of chivalry. Cervantes and Don Quixote are very dear to my heart. I'm very much a throwback to the old times. I was born way too late. I'm more realistic now; I used to be a dreamer. I'm working at getting that back!