Betting on the Pain, not the Pratfalls

Heather Headley talks her game-changing performance as Stephen Sondheim's Witch

Two years ago City Center ended the 2022 season of its Encores! series with Into the Woods, Stephen Sondheim and James Lapine’s “And What Happened Then?” re-envisioning of classic fairy tales. The show is always a crowd-pleaser, but there was something special about Lear deBessonet’s production, a poignancy and a delight that leapt like wildfire into the crowd every night. I’ve never heard an audience cheer like they did after that show.

Among the many outstanding performances from the Woods Encores! star-studded cast—which included Sara Bareilles as the Baker’s Wife, Neil Patrick Harris as the Baker, Denée Benton as Cinderella, Gavin Creel as the Prince, Julia Lester as Little Red, Ann Harada as Jack’s Mother, Annie Golden as Cinderella’s Mother, David Patrick Kelly as the Mysterious Man, and Kennedy Kanagawa as a showstopping Milky White—two years later the one I can’t stop thinking about is Tony winner Heather Headley’s haunting and often downright scary interpretation of the Witch.

Originated on Broadway in 1987 by Bernadette Peters, the Witch has lived ever after in the immense shadow of her interpretation. New actors have each added their own flavor to the role and found moments of their own, but Peters fundamentally defined who that character is and the comic sensibility with which she should be played. Her performance was so iconic, in fact, I’m not sure anyone imagined it could ever be done radically differently.

Then Heather Headley came to the stage and delivered a version of the Witch that was searing, tormented, and genuinely frightening, all while not breaking the overall feeling or shape of either the character or show. Indeed, her exploration of the Witch was so revelatory, it immediately became definitive itself. A more comic interpretation seems thin now in comparison.

I reached out to Heather early this summer to see if she’d be willing to talk about where that performance came from. Late last month we talked for an hour about her fear of Sondheim, the gifts of doing a role for just a short time, and how the pandemic and arguing with her kids helped her find her Witch.

This interview is edited for length and clarity.

Heather, thank you so much for doing this. Were you someone that had wanted to play the Witch for a long time?

You want the truth? I had no intentions, no wants, nothing to do the Witch.

Between me and you and all the people that read this, I was—was being the operative word—not a huge Sondheim fan. When I was in college I literally ran from him, and then ran from him my entire career. I think it was because Sondheim was just always so complicated. Sondheim is like *sings* E… D… many notes that are all over the place and really complicated…C. That’s him.

I’m a C major chord girl: E D C is how I like it. Flaherty and Ahrens, Tim and Elton, they’re for me. I love that kind of stuff.

And musically, Sondheim is so specific. You cannot play around with it. You can’t fake Sondheim. You can’t go in and be kind of sharp or flat, or be like That wasn’t the note, let me sing around it, because by that point the orchestra has gone and left you.  

People would say, You want to do Sondheim? You can get five million dollars per note. I’d be like Uh, No thanks, I’ll just live on ramen, it’s okay. I literally was, I think, scared of it, of doing it wrong and not understanding it.