Interview: Heather Headley Muses About Into the Woods, Parenting, and Her Role as the Witch

Headley leads a starry cast in the Encores! limited run of the Sondheim classic at New York City Center.

Heather Headley didn't enter showbusiness to become a superhero. Nor did she anticipate becoming a patron saint for musical-theater devotees. But after winning a Tony and a Grammy, and landing a slew of TV roles, she's embracing it all with even more gratitude.

Like many artists, Headley used the unexpected pause of in-person programming to reflect and reaffirm how much the arts are a dynamic and integral cornerstone of our lives. She is back onstage in New York City Center's star-studded Into the Woods as the Witch, full of anger, sorrow, and in the end, humanity. She's the kind of performer who makes you feel lucky to have seen her in whatever role she chooses and to be in communion with her.

Headley spoke with TheaterMania about connecting as a parent with her character, relating to audiences at New York City Center, and honoring Sondheim's legacy.

Heather Headley in Into the Woods
Heather Headley in Into the Woods
(© Joan Marcus)

This conversation has been condensed and edited for clarity.

I've seen you in two musicals, Into the Woods and The Color Purple. I found your performances unique and done through interpretation rather than concept. Please walk me through your process for Into the Woods.

I think [the character and I] meet in the middle because I bring some of myself to my interpretation of the world and what the script is saying. And then I know that the characters bring so much to me and teach me. I learned so much about love, becoming a woman, and sacrifices with Aida. I think Shug [in The Color Purple] brought a few things to me as well. But if we're talking about the Witch, I depended on motherhood to meet her halfway. The rest was whatever Mr. Sondheim and Mr. Lapine had to say about the character.

Obtaining tickets to Into the Woods has become a status symbol of sorts. Do you have moments of, "Oh God, I have to make sure that people aren't disappointed"? Does the Encores format make it more challenging to have the mental freedom to relax?

I was just sitting here thinking, "OK, go through your lines. OK, do you remember your words?" I always think I have to give people my best every night. If I coast, I might forget a line. The Encores is fun but more challenging because you only have two weeks of rehearsals. If I'm doing another show, I've got maybe four to six weeks in the rehearsal room and two of tech. I cannot think of a better group of people to pull off Sondheim and pull it off as well as they have within the allotted time, so you need a highly skilled group of people. You have Sara, Gavin, Denée, and Julia, who every day came in 80 percent better than they were the day before. So it really was just the right group to do it.

Is the comedy a vital part of how you get to your serious story at the core of Into the Woods?

That's life, isn't it? We have all this serious stuff going around. But sometimes, if we could look at it from the outside, we'd giggle about certain things. I always think some of the best comedians are the guys who can make serious things funny. Sondheim wrote a lot of levity into his work. Some lines are funny amidst the seriousness of it all. It wasn't necessarily that I'm trying to find funny moments to be like, oh, let's go out and be funny. When you play opposites, Neil or Sara or Gavin, it just naturally kind of happens. And I think for me, too, with this character, I've found some humanity in her because every human has funny moments. I necessarily didn't want people to like her but to understand her. She's not vicious all the time.

Heather Headley in Into the Woods
Heather Headley in Into the Woods
(© Joan Marcus)

Often artists discuss what the theater does for them, but what do you feel like you do for theater?

The past two years have made my feelings about the theater heightened. I remember the first time I had to sing after things improved and people in the audience were masked. The fact that we could go to a theater and stand in front of people and sing and kind of spit on the front row, and you could stand backstage with your colleagues and hug them and talk to them and not have to go to get tested every two or three days. If anything good has come out of that five-letter word I won't say [she starts singing "We Don't Talk About Bruno" from Encanto], it's the fact that it taught us so much about humanity, vulnerability, and gratitude to bring that to our performances.

I'm not trivializing the pain, the hurt, and the loss, but when it comes to the theater, we stand there differently, with more humility. And I'm very mindful that there are people who have gotten bad diagnoses in that room. Some people are maybe not in happy marriages who've had a breakup, and who maybe are coming here to get their minds off of things. Both things are heightened for me, especially during the past few years when we were trying to perform for our children.

The kids keep you humble.

Yes! [laughs]

You play a parent in this musical, and you are also a parent offstage. What are the most challenging things about working in theater and being a parent, and do you feel that that has evolved since you first became a parent?

This has been true to some extent because I'm on my own. We live in another state. At first, my husband came here and was like, "Go in, do a week and a half, get rehearsals under your belt, know what you're doing. And then we'll bring the kids." It wasn't feasible for them to come in because of all the restrictions with that five-letter word and theater. I tried going home, but a storm stopped it from happening. There's FaceTime, but it's been three and a half weeks, and I haven't seen my children. That has been tough, even though I've wrapped myself up in the show and taken the time to figure out what I was doing and just do the work. My oldest son is coming in on Thursday!

The theater then becomes your family since most of us come here from somewhere else. These people that I just met have been so kind, embracing, and sweet. Sara and Gavin are just trying to keep me here! [laughs]

As an audience member, one of the takeaways I had from Into the Woods was celebrating the endurance and strength that comes from being a parent and the endurance needed to be a parent. What is the message of the show for you?

You're right about the parenting message, and not everybody does it right. What are we acting out for our children? And what am I teaching my group and not necessarily by what I say but by who I am? Children will see, they will learn, so be careful about what you say and be careful about what you do. I think the overlying thing is about how we're going to send these children out into the world, into these woods. How did we handle the past two years? We all want to be loved. I hope in the years to come, my children will say to me, "Mommy did OK during that time."

Neil Patrick Harris, Sara Bareilles, and Heather Headley in Into the Woods
Neil Patrick Harris, Sara Bareilles, and Heather Headley in Into the Woods
(© Joan Marcus)

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Into the Woods

Closed: May 15, 2022