"Why Would You Take a Child?": Heather Headley Talks Into The Woods
How her children, her fear, and a bad pair of shoes helped Heather Headley find greater depths in Stephen Sondheim's famous 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.
So my agent Joe Machota called me a few years ago and said The Muny is doing Into the Woods, and they want you to be the Witch. I was like, Absolutely not. No way.
And there are some things that Joe believes in, and he just won’t take no for an answer. He said, I think it’s a good thing, the Muny’s great. Unless it’s about your children or your schedule, you’re doing it.
So there I was literally studying the music as if I was in school again. And then, like 5 or 6 years later they asked me to do it at City Center Encores!
So no, there was no thought in my mind, Let’s do Sondheim! But [having done it], it’s like when women have babies: You go through it, and the labor is very intense, and you’re like I can’t do that, and then you do, and you’re like, I did that.
And now they won’t stop calling me. I had to sing “Move On,” and I was like, I like this too!
I think it was one of these things, maybe he reached down from Heaven and he was like, It’s time you and I had peace. It’s time you and I came to a kind of a truce.
I like the fact that I came to it at this point in my life. I maybe needed the time, the age and maturity to see it the best way that I could.
Okay Sondheim, you and I are friends. We’re good.
Going into it the first time at the Muny, how did you work through your apprehension?
One of the things I love about Gary Griffin [director of the Muny production] and definitely Lear is that they allowed me to find the Witch, my Witch, on my own.
I think the beauty with the Muny and the Encores! stories is that they’re only for a certain amount of time. So you really can try new things, and kind of go, Well, if they hate it, I’m done in two weeks. My career is fine; by the time they hate me, I’m leaving town. *laughs*
So there’s this part of you that says just go for it, be as exploratory as you can be. Whereas I think sometimes you’re more trepidatious maybe if you know the show has to sit there and then they hate it for nine months.
So Gary and Lear allowed me to find this life that I wanted for her. I’m incredibly grateful for that.
Your take on the Witch is the first version I’ve seen that doesn’t seem informed by Bernadette or her comedic instincts. Your Witch felt like a woman in pain.
Here’s the thing: I get these characters, these women, and you want to play them as well as you can, right? When I got the Witch, I’m thinking, Well, she’s the bad guy. My head kind of went there, that she’s the bad guy.
But as I’m reading it that first time, I found that Sondheim did a pretty interesting thing, in that he told everybody she’s a witch, but he never says, is she a good witch, bad witch, evil witch? Nothing. He just says she’s a witch. Us as an audience, everyone in the show just takes it for granted that she’s a bad witch.
And going through it, I thought to myself, I don’t think she’s done anything wrong. Now is she the best mom? No. Am I the best mom? No. Does she have a little anger problem? Maybe. Do you want to invite her over for dinner? Maybe not. *laughs*
But nobody’s talked to her. The Baker lives next door, and he’s been there for maybe 18 years or more, but for however long he’s lived there, he’s never come over and said, How you doin’? His dad told him she’s a witch. But did you come over here to figure out if I’m a witch? No, you didn’t. I am, but you didn’t. In his eyes, she’s just a bad witch.
I think she’s lonely even before she’s turned into the ugly witch. Because the thing she asks for from the Baker’s Father is the baby. She doesn’t say Come over here and wash my car every day, or Come over here and I will do this to you. She says Give me your baby. I think she’s lonely and she wants to be a mom.
Then I was talking with my kids. The first time [I played the Witch] I’m a mother of 2 kids, the second time, with Lear, I’m a mother of 3. I remember sitting with them and I said, Who’s to blame? Who’s fault is it? And one said, Well, it’s your fault, Mom. You did all of this. One of my sons was actually quite upset. He said, You’re the bad guy. You’re the bad guy!
And I said, No, I’m not! I’m not the bad guy. And they were like, Well, She did this [to Rapunzel’s Prince], and I said, She never plucked the Prince from the tower, he fell because he was climbing up a tower for her daughter, he fell and hurt his eyes. Well, you put her up in a tower, Mom.
Headley with sons/dramaturgs Jordan and John in the New York Times, a year after the MUNY production.
And I remember thinking, just a few years ago I was told by the entire world to lock my children up in a tower, and that I would be ridiculous and stupid if I left them outside. In fact I would be vilified if they came outside, because there was a giant in the land, called Covid. I remember talking to Lear on FaceTime about that. And it just hit me, I’m doing the same thing the Witch does. Hence another reason why I kind of doubled down on Am I the bad guy? No. I’m just protecting my children.
So I think she’s a mom. And I think she’s sad that nobody has come to see her, and she’s desperate because she’s seeing that her child is growing up and asking questions. You know when you start growing up and you’re starting to move away from your mom, she’s not everything you need now. So Rapunzel is trying to fly the coop, and the Witch is like, I need to get myself together. If I get beautiful again, maybe…?
So for me, there was no hilarity about my Witch. There was no funny for her. There was only sadness, desperation, loneliness. I have three days to get myself together, and if you don’t do this for me, I’m done.
So would you say she wants to get herself together because she thinks then Rapunzel will stay, or she thinks then she’ll have more of a chance of connecting with everyone else?
I think both. The first person she goes to after she’s made whole is Rapunzel. She goes to find her and she goes Look, it’s me. Look what I am! That’s interesting. She doesn’t go, Hey, everybody! The first order of business is to find her daughter and say Come on, we can be a family now, see? I’m not that bad, right? And at that point the relationship is severed.
Remember, as the Witch she’s got power, and in her beautiful state she has nothing. She’s ordinary. That was something I also had to think about: Why trade? Because to me when she’s the Witch, there’s a certain amount of confidence as well. There’s a confidence to walk into your neighbor’s house and say, You’re going to do this for me, because I told you so.
Then the opening of the second act she’s like, Oh I’m scared, what was that? *laughs*
I honestly never wondered why she took Rapunzel instead of punishing the Baker’s parents in some other way.
Headley rehearsing part of “Stay with Me” with Shereen Pimentel (Rapunzel) at City Center.
A lot of people say she’s so mean because she took the Baker’ Father’s daughter. And I was trying to see it the other way: Why would you take a child—to be mean? Why would you lock her up in a tower—to be mean? But then you tell her that nobody would love her like you do, and you bring her everything. Why would you do that?
At any point the Witch could have been like, Get out of here, go tell you daddy to come over here, or Every year he’s supposed to bring me $5000 and two cows, or something like that. She never does. She keeps the child.
It just instructed me that she was lonely.
But in order to play it that is way I felt as though I needed—I always say—every “i” crossed and every “t” dotted. I needed it to make sense to me and to this audience who have seen it a certain way for all of time. Here I was coming to the Encores! for these few weeks to say, What if we twist it a little bit? How does it work if we twist it?
And I was definitely grateful to Lear and to Gary, to say Yeah yeah, let’s go that way. Trust me, if something was wrong, they would say they don’t think that’s the right thing. It solidified my choice for her in that they were coming along with the journey, they were like Yes, yes, we get it.
What you’re saying is making me reconsider other things about the show. In the opening, she and Little Red are the only main characters that aren’t given a home on stage. In Red’s case, it makes sense because she’s traveling. Also her restlessness is part of her story.
But the Witch is left as an outsider, even though she is the Bakers’ next door neighbor and her issues are actually similar to theirs. She wants to be a good parent.
Suddenly the opening set design becomes a representation of the problems we’re going to find here. And it’s all being narrated to us, underlining that this presentation isn’t objective reality, it’s one person or people’s version. Their story.
That’s society, isn’t it? This is what people do in life. You hear, Oh this is the bad neighbor, and you never take time to deal with them. I think so many times in our lives that’s what we do. We just put this thing on people, and we never get to know them. There’s hurt going on right across the street, pain going on right across the street. And somebody who maybe who just wants to talk to you, and you can say hi.
So yes, she’s an outsider, but going through the same things that everybody does. She is one of them. And I think that’s why maybe she can see through all of it.
I think she is one of the better parents there, too. Yes, I locked my child up. But I Heather locked my child up, too. So am I a bad witch? I hope you’d say no.
The Baker's father never shows up to find his child. In the musical at no point does Sondheim say that the dad came looking for his child. I always thought that that was interesting.
Cinderella's dad and stepmom are terrible. The Witch’s mother, not good. But the Witch actually tries.
So yeah, I wanted all of that for her, because I thought that arc would be a little more gratifying for me, to take my Witch on that journey. And I’m so grateful and humbled that people saw that.
There’s a moment in the opening scene where the Witch talks about how she could have turned the Baker’s Father into a stone, a dog, a chair. Usually that line is a big comic moment, but there was nothing funny about your delivery. It felt like you were really considering what you could have done. It was truly menacing.
Do you know, that was a choice of mine. I remember sitting with Lear and saying, Can I try please not to make it as a joke? This is a thought-out moment, I’ve been waiting for 15 years, 16 years to come in here and talk to him, so it’s not funny. I could have turned his father into anything I wanted to and and maybe I should have. If I had I wouldn’t be in this situation. But I didn’t, so here we are.
The other thing is, I don’t know how to talk Bernadette. That diva knows how to make a joke. *laughs* It’s amazing.
I was like, I don’t know how to make a joke out of that, so let’s go the other way.
For just a taste of how scary and furious Headley’s Witch could be, check out this GIF from the MUNY production.
Honestly every photo of her from that production is filled with menace.
Headley’s Witch about to burn Jason Gotay’s Jack and Rob McClure’s Baker to the ground with her eyes.
Do you have a number or moment in the show that’s your favorite?
This is weird, but I think that whole end when Rapunzel comes in, her death. That was a pivot for me. “Stay with Me” was great, I love “Stay with Me,” but it was just pleading. I think because of everything that we’ve talked about, [the moment of Rapunzel’s death] was Here we go. Let’s see if our work worked. If we did this right, the audience will actually feel sorry for the Witch, they’re going to be on your side here, they’re going to feel that this is really sad.
Before that in the second act there was hilarity. I get to calm down for a little bit and just be Isn’t this fun, there are giants jumping about. But then there was that pivot, and it was Here we go. We’re in. From there out, she’s in a different mode. It’s the loss of child.
Was it harder at all playing the character in Act II, dressed like a “normal person”?
The Witch look was a little harder. Even in Lion King, my features were shown. This, they were going to kind of cover some of the things that I kind of depend on, my eyes and the movement of my face.
When a costume designer says I’m taking a lot of that away, you kind of go into yourself. You really go, What do I have? I remember standing in the mirror with Lear, and there’s this big dress, so you have to really overdo your body. The only things that are out are really your fingers. I remember thinking, Oh, it’s really all in my hands.
I did ask them for uneven shoes, to get my body off-center.
Really? One of your shoes had a bigger heel than the other?
Yes. I didn’t want to fake a limp, because I thought that will come off as fake. So I said I would like one shoe taller than the other. And it did get me off center, it was more authentic. Almost angering, too, because I could not walk properly. That helped a lot.
I think it was good to be covered, because that’s how the Witch is in that first act, covered with the sadness and the depression and the anger and all this stuff. So I think it’s right that she was not able to throw her arms out and show them anything.
You also do so many interesting things with the way that you sing and speak.
I really wanted that first act to be low and gruff. I think for me some of the scariest people are not people that come in and go *hyper cheerful* HI, HOW ARE YOU DOING?—I mean, some of them are scary, too, trust me, because you don’t know where they’re going with that, you’re like Okay, you’re crazy.
There’s a lot of energy there!
Yeah you’ve got too much energy. But there’s also that scary person when they come in and there’s just that low tone, that Before you were here, your father had a child. And it's like they know all the business, they know who I am. You’re in this Hidden Depths mode.
Also, I think sometimes when you’re not well, when you’re sad and depressed, your voice kind of lowers.
For the second act, I wanted her to be chipper, so her voice is higher. It’s like Hi! You remember me? It’s me! But I was like No, we’re going to make that whole first act really low and menacing.
You’re getting all my secrets!
Ha ha ha. I could ask so many more questions! But let me offer just one more. Beyond “Move On” at Ravinia last summer, have you done any more Sondheim since City Center? Or are there other Sondheim roles you’d like to explore?
You know at one point, Chicago Shakespeare, this is years ago, had called me in with Alan Cumming. This was with Gary Griffin again. They had us sit for two days and talk through Sweeney Todd.
And it was the same approach for me. I remember thinking, What would happen if a black woman was in England living in some kind of basement back in that time? Why would she be there? And what would drive her to make pies? Maybe nobody was giving her meat? Maybe I have to kill a few people because no one is giving me anything. So here you go. And why is she in love with this guy?
Schedules didn’t allow for us to put it up, but it was going to be a different take.
I think Sondheim kind of brings out that whole “Why does this look like this?” way. I love the fact that he tells us everything and yet he doesn’t tell us everything. So you can move through his work in different ways and find these different layers to it. That’s why I’ve fallen in love with it.
So yeah, it’ll be interesting if there’s anything else. Imagine this, from the girl who didn’t do Sondheim.
My nanny introduced my children to Sweeney Todd. They are 14, 9, and 5. And the 5-year-old has been going Attend the Tale of Sweeney Todd! Sweeney Todd! Sweeney Todd! I’m like, Oh no! *laughs*
Of all the musicals that they would fall in love with…. In the mornings going to school, my son’ll be like Can I play some music?, and then it’s Attend the tale of Sweeney Todd! The demon barber of Fleet Street! And I’m like Nooooo. Come and listen to some of The Lion King. Come here, work with Mommy. And he’s like No.
So that’s a big gotcha for Sondheim. He’s like If I’m not going to get you, I’m going to get your next generation. And he’s got them. He’s in my house. *laughs*
Thank you again so much for agreeing to do this.
It's funny, many times you go back to a role, and you say to yourself, Am I done with you? I think that’s the beauty with Broadway, every night you try to fix or beat what you did before. And there are some times you wake up a year later going, Oh, is that another thought?
I tried to leave everything on the stage with the Witch, but it would be fun to do her again at some point. I’ve kind of locked a little place up for her in case I need to open that Pandora’s Box again.
I remember looking at the audience at City Center, and people had their masks on, because we were still in Covid time. The giant was still outside. And there we were, trying to get through it. It was a great joy to work with Sara and Neil and everyone. I was so proud of them when they went to Broadway and did as well as they did.
I remember when Sara first sang “Moments in the Woods.” That’s when I fell in love with Sondheim, listening to her sing “Moments in the Woods.” I remember just thinking Aw, come on, that is beautiful.
So it was the best of times, and it was the best of times.
Thanks so much to Heather Headley for sharing her experiences playing the Witch, and to her and her team for not hitting delete when they saw an email from someone who wanted to know if she’d do an interview about a show she did years ago!
You can find Heather so many places, including on Netflix, where the fourth season of her show Sweet Magnolias is coming soon; anywhere you get your music; and cross your fingers, maybe in another Sondheim show sooner than later.
Next up at Theater Wow: My interview with scenic designer Tatiana Kahvegian for her Tony-nominated work on The Outsiders.
And because it helped her love Sondheim, here’s Sara Bareilles doing “Moments in the Woods.”