George C. Wolfe has always dared to eschew expectations.

When the director-playwright-producer-lyricist first exploded onto the Off-Broadway theatre scene in the mid-1980s, it wasn’t with a traditional project. “While attending NYU, I wrote a musical that in my mind was going to be a big hit, and a play that I wrote just for myself. The musical was not a big hit, and the play that I wrote, The Colored Museum, changed my life and my career.”

The Coloured Museum, which explored Black American culture through 11 satirical exhibits, was a firm success, with Wolfe almost immediately recognized as a prodigiously principled artist. In his episode of Playbill's My Life in the Theatre, available now, he looked back on just a fraction of his creative ouvre, with one major turning point leading to all that would follow. After The Coloured Museum had enjoyed extensive life Off-Broadway, on the road, and even across the pond, the pressure was on Wolfe when it came to selecting his next project.

Instead of the flashy offers thrown at him by the powers-that-be, Wolfe picked a distinct challenge: a bio-musical dealing with the complicated legacy of the jazz pianist Jelly Roll Morton.

Called Jelly's Last Jam, it was hardly smooth sailing during the development period; as often happens when genius collides, there was a battle of wills behind the scenes between Wolfe and star Gregory Hines. “When Gregory Hines and I first met to talk about Jelly's Last Jam, we didn't get along at all. But during our complicated journey as collaborators, I grew to love him in the role, and he grew to love it. We grew to love each other.” Wolfe pulled double duty on Jelly’s Last Jam, writing the book and proving himself as a director to the tune of two Tony nominations.

Over the following two decades, Wolfe rose to the top of the New York theatre industry, with five Tony wins and unrelenting acclaim. He also spent 12 years as the head of the acclaimed Public Theater. Then, in 2011, Wolfe suddenly found himself at a crossroads. That year, the abrupt closure of A Free Man of Color after just 61 performances nearly caused Wolfe to walk away from Broadway entirely. 

Thankfully, Joe Mantello and Daryl Roth hooked him back with a glorious revival of Larry Kramer’s The Normal Heart that filled Wolfe’s own heart with hope. “It was this miraculous event… all the cynicism that I was feeling about why I was even doing shows on Broadway anymore, all of that went away because of the electric energy that was happening in the Golden Theatre. It revitalized my belief that the marketplace can still handle subject matter that is daring and challenging and tough and smart.”

Today, Wolfe is still challenging norms and inviting his audiences to dare for more. His revival of Gypsy, starring Audra McDonald, has reframed the classic without changing a single word of Arthur Laurents’ original book. 

READ: Under George C. Wolfe and Audra McDonald, Gypsy Is Revisited Through a Black Lens

“There are these threads that run through your life–when I was in the NYU musical theatre program, one of the teachers was Arthur Laurents, and he was one of the people who championed me and my work very early on. It is so very fulfilling for me to now direct his work. The more shows you do, the more you find yourself inside the stories of the shows, and the more the shows help you become who you become. And you, hopefully, help them become what they're going to become.” In short, it’s all full circle.