By James Turano
The phone rings at precisely the appointed time, and Heather Headley’s voice is welcoming and warm, quickly breaking the ice with first-name familiarity before there’s even a chance to return the “Hello.” The lively, expansive conversation with Ravinia Magazine goes 15 minutes past the agreed time, all the while continuing with an audible smile.
It’s hardly a “diva moment,” even though that’s how she jokingly refers to herself. Yet if one uses “diva” in its original and laudatory definition—“a glamorous woman who is pre-eminent in her field”—then Headley is a diva of the highest degree. After all, she won a Tony Award for her show-stealing outing in the title role of Broadway’s Aida in 2000, then added a Grammy Award to her trophy case in 2010 for her gospel album Audience of One. She’s also appeared on many of the world’s praised stages, not only across Broadway and London’s West End, but also including New York’s Carnegie Hall and Ravinia Festival last summer, as one of the featured singers on a concert honoring the legacy of the late Stephen Sondheim.
Headley returns to Ravinia’s Pavilion stage on July 16 with an evening of songs from across her own stellar career to headline the festival’s annual Gala Benefit Concert hosted by its Women’s Board, where she reunites with the Chicago Symphony Orchestra. She is also joined by Ravinia Chief Conductor Marin Alsop and a chorus of special guests: singers from the Voices of Trinity Mass Choir and from the Ravinia Lawndale Family Music School, one of the dozen community-based Reach Teach Play® music education and engagement programs supported by the funds raised that evening.
The last time I interviewed Heather Headley, almost 24 years ago, it was the day before the first rehearsals for the six-week, pre-Broadway run of Aida in Chicago. The Disney-produced musical, based on the beloved Verdi opera and written by The Lion King songsters Tim Rice and Elton John, had a disastrous and critically lambasted 1998 premiere run in Atlanta.
Headley, however, was one of the few positive and promising elements of the original production.
Disney summoned Chicago’s Tony-winning Robert Falls to rescue the Egyptian love triangle. The Goodman Theatre’s adventurous driving force and former, longtime artistic director, Falls revamped every aspect of the show; wisely, however, he kept Headley in the lead role.
At the time, Headley was a budding talent and on the fast track to fame. She universally impressed as an understudy for Audra McDonald in the original 1996 Toronto production of the musical Ragtime. This led to Headley’s highly praised portrayal of Nala in the original 1997 Broadway presentation of the Tony-winning—and still-reigning highest-grossing stage musical of all time—The Lion King.
Heather Headley was star-ready.
In March 2000, Falls’s production of Aida opened on Broadway to rave reviews, and Headley instantly was christened a genuine Great White Way phenomenon. Aida went on to hoist four Tony Awards, including one for Headley as Best Actress in a Musical. In the last two decades, she’s recorded several albums, made further star turns in musical adaptations of The Bodyguard and The Color Purple, and expanded into dramatic acting, appearing on several TV projects such as NBC’s Chicago Med and the Netflix series Sweet Magnolias.
Fifteen years after her Tony-toting bows as Elton John’s Aida, Heather Headley made a triumphant return to Broadway as Shug Avery in The Color Purple, having hitched her star in the interim to making an equal statement as a concert and recording artist, winning a Grammy with her album Audience of One. Now both sides of her winning songbook feature in her concert program “Broadway, My Way,” which sees her back at Ravinia after a lauded outing last summer.
Born on the Caribbean island of Trinidad, Headley and her family came to the United States in 1989 and settled in Fort Wayne, IN, when her father became a church pastor nearby. Her musical leanings sprouted at a young age, as she sang with her mother, took piano lessons (“The greatest gift my mom ever gave me”), and later sang at church services and acted in church-related programs. Her talent was nurtured by a supportive group of teachers, which eventually resulted in a musical scholarship to Northwestern University.
Headley soon appeared in two local Chicago musical theater productions, and after completing her junior year at Northwestern, fate interceded.
Her first theatrical agent, Janet Louer, a Chicago theater veteran and Joseph Jefferson Award–winning choreographer, strongly urged a hesitant Headley to audition for the Ragtime understudy role. “I didn’t think she would get it, because she was too young, and she was still in school. But I told her, ‘Go. The industry needs to know you exist,’ ” Louer recalled. Headley dazzled the producers and won the gig, forcing her into a difficult decision: to leave Northwestern before her senior year, move to Toronto, and follow her dream.
Early in the Ragtime run, Louer remembers Headley nervously phoned her to report McDonald fell ill and that she would be going on that night. Within hours, Louer hopped a flight to Toronto and made it to the theater just before the curtain rose. “I had never met Heather. I only saw her photo. When the show began, there was an aura around her. I thought, ‘Wow, who is that? And I realized it was Heather. It was magical,” Louer recounted. “The next day, my phone rang off the hook. It was a game-changer.”
Speaking from her suburban Chicago home, where she lives with her husband and their three children, Headley fulfilled the promise of her transcendent voice and continues to make magical musical moments.
We spoke in 1999 and you told me the reworked Robert Falls production of Aida was giving your ‘friend’ a makeover and giving her some pretty ‘new clothes’ to wear.
Did I say that? [Laughs.] Well, the new clothes worked, didn’t they! I am grateful for that show and that character. Aida is still in me. She will be forever. I love her.
What can the audience expect from your performance at Ravinia?
I like to tailor programs to the audience, to the location, to the venue. Big songs that I usually bring to concerts, like “Can You Feel the Love Tonight?” and “Somewhere Over the Rainbow,” will stay in, but there may be some new picks. I do want to make this show special and different for Chicago and Ravinia.
What’s it like to perform with a musical force like the Chicago Symphony Orchestra?
The best musicians in the world are in the CSO, right? So it can be intimidating! I mean, they play Rachmaninoff on a regular basis! However, we do get together beforehand, and that’s where the conductor comes in, to lead us into the emotion of it. Performing with the CSO, I think, is like hopping a train. Because as a performer, when you get that timing right, that train will take you to the most beautiful places. It’s gentle at times, it’s fast, it’s powerful, it’s calm again. It will even change your world standing still and feeling that power. But if you jump at the wrong time, with something that powerful, it will run right past you. So, it can be frightening, but it is also exhilarating.
And what of the musicians of the CSO timing up with your locomotive-like talent?
I’m honored if the CSO thought thinks way about our performing together! I have had some members of the orchestra tell me how much fun they have had working with me. When people of that caliber compliment you, it means so much. I will have to bring my ‘freight train’ to match them. When you play with the CSO, you have to bring your A-game.
How do you choose the songs to perform?
I see songs like dresses. Like something I’d like to try on. I’d like to do some songs sung by men. I like to try on many different ‘new dresses.’ But sometimes the dresses don’t fit! No matter how good the seamstress is, I can’t squeeze into it … the song just isn’t right for me. But we do try to ‘take it in’ a little here, or ‘cut the sleeves’ there, to see if it will ‘fit.’ And that’s always fun to explore. If it doesn’t work, I’m still happy I tried it on.
Any memorable ‘dresses’ that have caught your eye?
I was in London when I was nominated for an Olivier Award [British theater’s equivalent of Broadway’s Tony Award] a few years ago, and during the program, Tim Minchin, who wrote the music for the stage musical Matilda sat at the piano and sang “My House” from the show. I grabbed my husband Brian’s hand and I told him, ‘I’d like to try that on to see what it sounds like.’ I love those songs you can take out of the context of a musical show and they still resonate. And so, I did. I tried it on. We did make a few alterations—cut some things, moved others around—and it worked out. It’s been a beautiful song for me to sing. That’s how I feel about The Sound of Music, I would like to ‘try on’ Maria just once and get it out of my system!
You have won a Tony Award and a Grammy Award, all you need are the vowels—an Emmy ‘E’ and an Oscar ‘O’ to attain the coveted ‘EGOT’ status.
Yes, leave it to me to have just the consonants; can’t spell a word without a vowel! We’ll see, maybe.
It must have been quite a culture shock to move from Trinidad to Indiana.
Every single bit and more of a culture shock. It was a different country, a different climate, a different accent, different food, different topography—everything was different. We landed in October, and in November I wrote back to my Trinidad friends that I had made it through the winter. I had no idea how long winter was here. But I am grateful I came to Fort Wayne first rather than going to a huge city like Chicago or New York right away. Fort Wayne was a gentle entry for me. I may perform in Trinidad soon. I would like to introduce my children to where Mommy is from.
Your career has taken you to many places and in many directions. Has that been by plan or serendipity?
There has been a bit of both. I always have ideas of what I’d like my life to be. I am a Christian, and I do pray on things. And God has outdone any dreams I may have had. My dreams for me are not as big as His dreams are for me. But I also have been discerning about my projects. I turn things down. I tell young people it is okay to say no because sometimes a no can lead to an amazing yes—a new opportunity you never expected. I get to do what is instinctual for me. I never call it work; though, yes, sometimes it is work. I like to think I’m ministering. Let’s go minister to some people with music and make them happy. ■
James Turano is a freelance writer and a former entertainment editor, feature writer, and columnist for national and local magazines and newspapers. He has written official programs for eight Elton John tours since 2003 and is also a Chicago radio personality and host on WGN 720AM.