Athough he is an Academy Award-nominated movie star, Jake Gyllenhaal has always been a fan of musical theater. In the summer of 2015, he starred in a four-night run of Little Shop of Horrors and then, in October 2016, another four-performance stint of Stephen Sondheim’s masterpiece about the clash between love and art, Sunday in the Park with George.

“Performing Sunday in the Park was something like pure joy,” Gyllenhaal told me, calling from his apartment in Manhattan before heading to the Hudson Theatre, where he was about to start a tech rehearsal for the newest production of Sunday in the Park, which will open on February 11 until April 23, 2017. “The short run was too short of a time for joy to be on stage,” he continued. “I wanted to prolong joy, so we’re back. They didn’t have a hard time convincing me.”

What’s the first musical you remember seeing?

Anything Goes at Lincoln Center. I was four or five years old. I remember thinking that the opening number was incredible and then I fell asleep, so that’s all I remember. The first musical that really resonated for me was The Secret Garden. I was around 11 years old. Secret Garden is my mother’s favorite musical. It was a great inspiration for her. My mom is the musical theater guru in our family: She represents a bastion of hope in a group of cynics. My mom had been banging down my door for a long time to get me to do a musical. This production of Sunday in the Park is the closest thing to my heart of anything I’ve done in a long time.

In the film Demolition, which came out last year, your character dances through the streets of Manhattan. I watched it around 3 a.m. recently, and your dancing made me both laugh and cry.

Cry? Really. Before I did those scenes, I felt like crying. [Laughs.] I’m one of those people who believes in good terror. The terror that inspires! Having a fear and facing it is always illuminating. On Demolition, I said “yes” to the dancing. I was pretending to be an actor who isn’t scared of dancing around New York. That wasn’t really true. I was terrified.

Did people recognize you on the street?

Not really. New Yorkers have seen it all. But, at one point, I was dancing in the middle of Church Street and two buses crossed by simultaneously and both drivers leaped out their windows and said, “Hey, you ass—” and then they saw it was me and said, “Oh, hi. Could you dance somewhere else?”

Little Shop of Horrors was your first performance in a musical. Did you find it addicting?

It was the first time I had sung before a paying audience since high school. It was a dream, especially because I was performing opposite the amazing Ellen Greene, who had originated the lead character in the original production of Little Shop. For me, it was a romantic, sexual fantasy come true.
During the run of Little Shop, I received a lot of encouragement. And that gave me more incentive to think about doing another musical. In the world that we live in now, encouragement is vital. Not just for actors—these days, we all need encouragement.

Had you sung Sondheim before?

In high school, I was in West Side Story. I played Riff, the leader of the Jets. But because the music in West Side Story is Leonard Bernstein and Sondheim, I don’t think of it as pure Sondheim. West Side Story was a warm bath. Sunday in the Park is a super-hot fire: Sondheim at his best and most intimidating.

In the video, directed by Cary Fukunaga, you perform “Finishing the Hat,” which is a particularly complicated song from Sunday in the Park.

Yes, we thought about an easier, shorter song, but why not pick the most difficult song! [Laughs.] We did five or six takes of me onstage at the Hudson Theatre. We wanted the video to feel imperfect. Cary was dangling from a wire hanging from the top of the theater and I am on the stairs trying to remember every word of this amazing song. It was mad. But that’s why it was so fun.

Gallery Links:
Sunday In The Park With George (2017) > Jake Singing ‘Finishing The Hat’ [Rehearsals] (Behind The Scenes)