5 Questions With Cuba Gooding Jr., Chicago's Newest Billy Flynn

Cuba Gooding Jr. has nothing to prove. He's starred in enduring classics like Jerry Maguire, for which he won an Oscar, Boyz n the Hood, and Snow Dogs; received an Emmy nomination for playing O.J. Simpson in American Crime Story; and even proved his stage chops opposite Cicely Tyson in The Trip to Bountiful.

But this week, Gooding Jr. is boldly going where he's never gone before. Bayou Caviar, the first film he's ever directed, hits the big screen October 5, and on October 6, he returns to Broadway as Billy Flynn in Chicago. Though it's his musical-theater debut, he's no stranger to the role. He played the "silver-tongued prince of the courtroom" earlier this year in the musical's London revival, to great acclaim. Now he's ready to razzle-dazzle New York City, and he's looking forward to the full-circle emotional experience that will come with it.

1. Why Chicago?
I wanted to see if I could pull off a musical. That was the main reason. I love the music of Chicago. There are certain numbers I can listen to over and over again. "Mr. Cellophane" is probably still my favorite. There's something so sweet about it. "Razzle Dazzle" is fun, too, and I do a little modern dancing in it. And "We Both Reached for the Gun" has that big note at the end.

2. You did 158 shows as Billy Flynn in London earlier this year. How scary was that first night, and did it get easier?
I don't know if I'd ever use the word "easy." But it definitely is something where you have to be so focused and concentrated every single moment of the day. I was across from Ruthie Henshall, Josefina Gabrielle, and Sarah Soetaert, who are the royalty of the London stage, and that really kept me on my toes. Doing eight shows a week, six days a week, was a real kick in the pants for me. I can't wait to be in that space again.

3. How is doing Chicago different from doing The Trip to Bountiful?
Trip to Bountiful was an emotional release. Towards the end, I felt like I was having a nervous breakdown. Dealing with grief and loss and family and mortality…it really drained me. What's great about Chicago is that the band is onstage behind you. You have the orchestra pulsing through your body. When it starts to click together, it really is a magical thing. It never got old after four months of doing the same show.

4. You recently directed your first film, Bayou Caviar. How has the experience you gained in that position influenced your subsequent acting roles?
As an actor, you interpret a character to the best of your ability, deliver that performance to the director, and hope they get it, and then you come back, sometimes a year later, and see if they did or if they didn't. As a director now, I question every little element of every little thing that I do. I don't just accept certain things. And I think that enriches my performance.

5. What are you most looking forward to about playing Billy Flynn on Broadway?
My family being able to see it. No one was able to get over to London, except for my two sons. So my daughter will see it, and my mom. Coming from a musical background — my dad and mom being singers — it'll be a full-circle moment emotionally.