For Heather Headley, Broadway continues to exert a special pull

The scariest performance of Heather Headley’s life fell on a Tuesday in 2000, two days after she won a Tony Award for her portrayal of enslaved Nubian princess Aida in Disney’s Verdi opera-inspired Broadway hit of the same name. While she was no stranger to the Great White Way, having previously appeared as Nala in “The Lion King,” this was her first leading role in what would soon be one of the most storied musicals in history. Though it happened half a lifetime and numerous career milestones ago, not surprisingly it’s still fresh in her mind. 

“Everybody else was like, ‘You have a Tony. Put your shoulders down,’” says Headley — who also won a Drama Desk Award for the same role — from her longtime home base in suburban Chicago, where lives with her husband and their three children. “And my shoulders went up, like, a foot. Because all of a sudden, you’re in a class of not many people. You’re in the group with Patti LuPone and Bernadette Peters and Audra McDonald. And from that point on, the moniker ‘Tony Award winner’ follows or precedes my name. For the rest of time, people go, ‘Oh, well, let’s see.’ And so now you have to live up to that.” 

When Headley visits Symphony Center on June 3 to perform selections from her extensive Broadway and pop repertoire with the Chicago Symphony Orchestra, the Tony winner in her will be accompanied by the four-time Grammy nominee who won the award for best contemporary R&B gospel album for her “Audience of One” in 2010. And the television star, too. Now in her fourth season of the Netflix hit “Sweet Magnolias,” Headley and her cast will return for a recently announced fifth season in the not-too-distant future. Broadway, though, retains a special place in Headley’s life, and not only because so many aspects of her success grew from those celebrated early years.  

Even during her undergraduate studies in the music program at Northwestern University, Headley felt limited by the classical genre. Learning operatic techniques and arias, she says, was vocally valuable in the way that balletic training is physically valuable to all types of dancers. But growing up in Trinidad before moving to Fort Wayne, Indiana, she was exposed to a wide variety of music — from classical church standards to Bollywood showstoppers — and loved to sing it all.  

“I remember when I started operating at Northwestern, I gave my teacher a lot of trouble,” Headley says. “Because I’ve always been one to say, ‘I want to sing everything.’ And that’s what this show is. It’s me going, ‘I want to sing a little bit of everything.’ I like having all these dresses in the closet that I call songs, and let’s just try them all on. But [my teacher] said to me, ‘Well, we’re going to train you for opera,’ and God bless her. I ask her forgiveness now.” 

Headley also remembers thinking that opera singers typically don’t blossom until they reach their 40s or 50s, and she wasn’t about to wait that long. Besides, by her own estimation, she’s far better built for Broadway and pop in terms of the way she hears music internally and interprets it externally. Playing around with pieces and putting her own spin on them rather than hewing to centuries-old tradition is more her style. 

“Nothing against the opera. I just think when I found Broadway, or when she found me, it was just this beautiful marrying of the theatrical side, the singing side, the dancing and movement of it, and the speaking of lyrics. In operas, you’re singing all night. I love the fact that in musical theater, when you can’t sing anymore, you speak. When you can’t speak anymore, you sing.”  

On June 14, Headley is scheduled to deliver the convocation speech at Northwestern’s School of Communication, from which she graduated nearly three decades ago. She revealed no specifics about her address, but she offered some insight that students would be well advised to consider as they leave college and begin their own professional journeys. 

“I compare myself sometimes to a horse, maybe a racehorse, and I have blinders on,” Headley says. “And so all I do is put my head down, and I’m like, What do you need me to do? I don’t think I looked up until later. Just keep doing the work. Keep the blinders on.”