Heather Headley: "Naked" On Stage

HEATHER HEADLEY BRINGS HER REMARKABLE VOCAL TALENTS TO THE MAHAIWE

By: Dr. Joshua Sherman

Photo By Megan Shuptar

July2026

Read Berkshire Magazine's July 2026 Issue.

Heather Headley first rose to prominence originating the role of Nala in The Lion King on Broadway before earning a Tony Award® for her star-making performance in Elton John and Tim Rice’s Aida. Since then, she has built a multifaceted career across theater, recording, and television. On Friday, July 31, at 8 p.m., the Tony® and Grammy® Award winner will bring An Evening with Heather Headley to the Mahaiwe Performing Arts Center in Great Barrington for a concert spanning Broadway, R&B, gospel, pop, and personal storytelling. Here are excerpts from our recent chat:

You originated the role of Nala in The Lion King and Aida in Elton John’s Aida. Can you talk just a little bit about the process of originating and developing a new role—and the challenges it presents?

It’s such a blessing, because a lot of people don’t have that opportunity to originate a role. It also comes with great trepidation and anxiety and a little bit of righteous fear, because you’re creating this role for the first time. There’s a stamp that you put on it that remains forever. It really is how you see the role, how you and the director see the role, how you feel the role, how you sing the role. It’s a beautiful experience, but it does come with responsibility, because it goes into history and into how the public and critics receive the character—all because of how you play it. It’s kind of like having a child. It’s amazingly fulfilling and great, but it comes with complexities and fears and anxieties.

There’s a very different pressure that comes with stepping into roles in which audiences have existing expectations. In 2001, you were Lorrell in the iconic Dreamgirls benefit concert with Lillias White and Audra McDonald and Billy Porter. In 2012, you stepped into The Bodyguard, filling Whitney Houston’s shoes in London’s West End. Then Shug Avery in The Color Purple and the Witch in Into the Woods at City Center. These are all iconic roles. So, when choosing roles that you’re excited to play, how do you bring your unique self to the role while also meeting audience expectations?

Well, you just kind of scared me listing all of those. (Laughs) I don’t know which one is scarier. Maybe originating a role has less fear, because people haven’t seen it before, so you’re introducing them to this person and hoping they’ll like her.

But all those other roles you just mentioned—people had done them before. You’re talking about Bernadette Peters and Vanessa Williams and Whitney Houston and Loretta Devine. You’re trying to figure out, “How do I bring my unique take on it and yet not hamper the work or make it any worse?” You don’t want to do that. I cannot be Bernadette Peters. I cannot be Vanessa Williams. I don’t have that gift—they have a completely different thing thanI do. So, therefore, you have to think, “What does my Witch look like? How does the Witch fit into my body?” Especially drawing from life experience and who you are and what you think, and then bringing that to the table. It has to be good enough that the

audience goes, “I understand what you’re doing. Maybe I don’t like it as much, but I understand it, and I’m there with you.”I think I felt that mostly with the Witch. Whitney’s role inThe Bodyguard was very scary for me, because I’m a huge Whitney fan. I loved Whitney Houston, so hers was almost trying to make sure we did justice to her work. With the Witch, though, it was more: How do I see this differently? What different things do

I bring to it? Not just changing it for the sake of changing it, because if it’s not broken, you don’t need to fix it.

You’ve had a successful recording career, receiving several Grammy® nominations and winning the Grammy® Award for Best Contemporary R&B Gospel Album in 2009, and many audiences also know you from television as a regular on Netflix’s Sweet Magnolias. Those are not only different media, but very different routines. The routine of doing a Broadway show is very different from a concert tour, which is very different from the recording studio, which is very different from television. How do you organize your life around those different routines—especially as someone with a family?

This is incredibly insightful of you to ask and understand. I consider the different mediums to be like children, and I love the kids. I have a firstborn that I maybe like a little more than the others. I think that’s singing. That’s my firstborn. If you ask me to pick a kid, I’ll maybe pick that. But on any given day, I might tell you I like one more than the other. There are days when you’re on Broadway and your voice is incredibly tired and it’s only Wednesday, and you wake up Thursday morning and think, “I don’t know if I can do this tonight.” When I did The Bodyguard,I don’t think I spoke to my son before 6 p.m. for maybe seven months, because I was just trying to save my voice. I would stay in bed and just wait for the show, because it was such a hard thing physically. Then there are days when your call for Netflix is four o’clock in the morning, and you’re like, “No, I don’t like this kid today.” You’re there until midnight—and television is such a different beast. You’re not doing scenes in sequence, and because I’m from theater, I love an arc. I want to feel the sequence. So, if you’re doing Scene 4 and then jumping to Scene 20, your brain has to wrap itself around all of that. Then there are the concerts, which kind of marry theater and music together. But there’s still that moment of waking up in the morning and thinking, “Can I sing?” Our kids—my actual children, God bless them—if they come downstairs and cough, I’m rubbing them down with Vicks and Thieves oil, because I can’t be sick. I still love singing the most.

I love walking into a theater and seeing an audience. And when I’m singing in concert, it’s me. It’s Heather. They’re all like children to me, and I love them all. I hope not to pick one, but there are days you like one kid more than the others.

Architectural Digest featured your coach house in 2020, which includes a recording studio and a home movie theater. First of all, it’s beautifully designed. Great taste. I would expect nothing less. But in the article, you specifically commented on the construction process, and you said, “I’m not great with the process. Even in my theater work, I’m all about the show. Rehearsals drive me crazy.” That was a very interesting comment, because most actors I’ve worked with are all about the process. I was hoping you could talk a little bit more about that.

Well, it’s funny that you bring up this house. I literally came onto our street this morning before this interview and kind of said, “Lord, thank you that we live here.” It’s just a beautiful piece of architecture. The guy who designed it designed our coach house, too—we call it the clubhouse—and my husband wanted to put a studio into it, and Sweetwater outfitted it beautifully. But going back to the rehearsal process, for me, I love performing because the audience informs me so much. I don’t believe in the fourth wall. I don’t think there is one. I think the audience is part of the show. They’re in the room with us. I find myself always looking into the audience and making eye contact with them, because that informs me. Whether it’s concerts or theater, it tells me how things are going. And so, in rehearsal, I’m devoid of that. I have people in the room who have maybe seen it 45 times already. The director, producers—they’re excited about the show, and they’re smiling because it’s their baby, too. But I don’t always feel as though I get the exact feedback that I need. Live on stage, I’m often entertaining Joe Schmo in the back who says, “My wife dragged me here, and I have no interest in being here, so I’m giving you two hours to figure this out—and make it worth it.” There are artists who are amazing in rehearsal or in the studio, and then when they get in front of audiences, they get scared and nervous and anxious. That’s not me.

Let’s talk about the music itself. You’re coming to the Mahaiwe theater in Great Barrington on July 31. What can audiences expect? Broadway? R&B? Gospel? Some new music? What does the night look like?

When a theater is intimate, and I can really see everybody’s faces—and it’s just myself and a pianist, I call them my “naked shows.” There’s no hiding behind an orchestra. There’s no hiding behind someone else taking over. It’s just us. I’ve got the best music director and pianist, Jason Webb. He’s just so great. The reason I bring him with me on these things is because he can make a piano sound like an orchestra. Because of his musicianship, I’m allowed todo all kinds of different things. So, we do alot of Broadway stuff. We do songs that I’ve always wanted to sing on Broadway but maybe never got to. We pull from the albums, too, because my singing career has always been a little schizophrenic. It’s because of the way I grew up. Growing up in Trinidad, I listened to Soca, Bollywood music, opera, classical music, gospel music, pop gospel music, R&B. I’ve never been someone who says, “Oh, I can only sing this.” I just love a beautiful song. If it happens to be a rock song, we’re going to figure that out, too. So, with Jason, I’m allowed to do different things. Especially when I figure out the audience, we can kind of shape things. I think they should just be ready for us to have a beautiful night together. I’m going to come into your living room, be as respectful as I can, and we’re just going to have a beautiful evening together and kind of walk through my career and the music. A lot of times with my shows, there are a lot of stories, because I like people to understand why I’m singing a song, what motivated me to sing it, why I wanted to try it out. Sometimes I see songs like dresses. I like to try some of them on. Some fit; some don’t. Some Jason has to hem, and then we go, “Okay, that didn’t work.” So, I love walking through the music like that. I hope they enjoy it and love it, but it’s always fun for me to be able to come and sing for people and have their minds cleared for the hour and a half or two hours that I get to be with them.

You’ll find that Berkshire audiences really love music and love a wide range of music, so you should feel free to try things out.

With orchestras, you send the set list two or three weeks in advance, and you’re not moving from that. It’s like standing in front of a train. You can jump on that train, and it’ll take you to beautiful places, but if you miss a step, that orchestra is going to run right over you. The beauty when it is justme and Jason is we can change things before the show. There have been times where I say, “Jason, I’ve been thinking about this song. Why don’t we try it out?” I love having these naked performances where it’s just us.

See Heather Headley at the Mahaiwe on Friday, July 31, at 8 p.m. Go to mahaiwe.org for tickets.