Heather Headley: a star with her feet on the ground | Caribbean Beat

Originally written for and published in Caribbean Beat magazine in 2012. The full interview transcript is published here, and at Discover Trinidad & Tobago.

In 2000, news spread about a Trinidad-born actress making waves on Broadway. Her command of her emotions made you sure that her onstage tears must come from some fresh real-world trauma.

The truth was very different.

“I would be in the moment, thinking of the journeys…Ten years ago, I was in Trinidad walking barefoot across the street to Miss Philips’ house to get some sugar, not thinking I would be standing on this stage playing Aida in Aida, with a Tony. OK, let’s cry,” she explains, laughing. “So it was emotionally cathartic because I could let everything out.”

Tony and Grammy Award-winning singer, songwriter and actor Heather Headley makes a tremendous impression in other ways too. It’s not just because of her beauty, cutting a slim, stylish and striking figure at five foot eight. Neither is it only because of her distinctive voice – a finely tuned instrument with a tremendous range of tone, colour and texture, equally at home belting out gospel and Broadway rabble-rousers, and lilting, lyrical ballads, all with startling dynamic contrast. What makes the greatest impression is how down-to earth she is, and her humour, intelligence, generosity and humility.

Heather Headley was born in Trinidad on October 5, 1974 to Hannah and Eric Headley. Her father was a pastor in Barataria, a little way outside the capital, Port of Spain, and some of Headley’s earliest musical exposure – and her values – came from singing and playing the piano in the church. She attended St Vincent Anglican Girls’ School and then St George’s College in Trinidad before moving to the United States, where her father was offered a job as a pastor in Indiana. She remembers her Trini childhood fondly – “I wouldn’t trade it for the world: the village, the community” – and credits Trinidad, and in particular members of her church and teachers at her schools, with nurturing her budding artistic talents, and making her believe that she could achieve anything. In particular, she remembers Standard Five teacher Miss Des Vignes, and groundbreaking women like Penny Commissiong (Miss Universe 1977) and Giselle Laronde (Miss World 1986).

In Fort Wayne, Indiana, she attended Northrop High School, singing with the Charisma school show choir, and starring as Fanny Brice in its production of Funny Girl. The move wasn’t all a song and dance, but: “There was always Mummy. She’s helped us during the toughest times and took the reins. And I don’t tell her enough, but she is a good mom,” Headley reminisces. “The other day, performing in Trinidad, I could not stand on that stage without thinking of Mummy, who was in the wings. And I think that’s where she’s always been – in the wings, cheering on.”

Ever the high achiever, Headley enrolled at the prestigious Northwestern University, starting as a voice major before switching to communications and even thinking of studying law.

But in 1996 she won a role in a Broadway-bound touring production of the musical Ragtime. From there she originated the role of Nala in Disney’s Broadway adaptation of The Lion King in 1997. Then she auditioned for and won the title role in Elton John and Tim Rice’s next Disney project, Aida. “She just blew me away,” said then-Disney CEO Michael Eisner. And it was Aida that fast-tracked the 25-year-old’s career, earning her coveted Drama Desk and Tony Awards, and a record deal with RCA. She told Jess Rosen, who negotiated the album contract, that she wanted not just a Tony, but a Grammy and an Oscar as well.

Her first Grammy-nominated solo album followed – This is Who I Am, which she described as “Whitney Houston meets Lauryn Hill”. This was one of many ways that Houston strongly influenced Headley’s career. “In my head, I wanted to be Whitney Houston, so me and my family didn’t know anything about Broadway,” she explained. In fact, her Trini family feared she was “working the streets”.

“It takes too long to explain, so I’m like, ‘Don’t worry. I’m a lawyer’.”

There was no reason for alarm: the debut album won her a slew of industry awards and nominations, with “He Is” and “I Wish I Wasn’t” hitting the top five on US dance and R&B charts.

Things were also blossoming in her personal life. In 2003, she married fellow Northwesterner and former professional football player Brian Musso. He’s been properly integrated into her family, first and foremost through food.

“I remember the first time we went to Trinidad, Brian sitting in the kitchen and saying, ‘You know how to make this? You need to learn!’” she recalls, laughing. “And I have always been, ‘I am woman, hear me roar! I do not need to be in the kitchen! I will never learn to make callaloo and pelau!’ But it’s been fun to learn to cook like that. My pelau still looks a little bit like coo-coo, and last night I made a bad callaloo – terribly bad – but I’m still eating it like it’s the best thing ever.”

Headley’s ever-growing legion of supporters had to wait until 2006 for her second album, In My Mind. Once again it was produced by industry leaders, including Jimmy Jam and Terry Lewis, Ne-Yo, Warryn Campbell, and Lil’ Jon. The title track climbed to number one on the dance charts. But it was her next album, the gospel-infused Audience of One, which brought Headley her first Grammy (and two nominations).

Her stature as an actress and singer firmly established, Headley added the role of mother to her portfolio with the birth of her son – “Commander General” John David – in 2009. Despite taking some time out to enjoy being a wife and new mother, Headley still toured internationally with popular classical singer Andrea Bocelli, which included two concert recordings: Live in Tuscany, for PBS, and the Under the Desert Sky CD/DVDs.

The past three years have also brought two personal and professional highlights. The first was singing a duet with Josh Groban at the 2009 inauguration of US President Barack Obama on the steps of the historic Lincoln Memorial.

The other was a charity gala, Home, she headlined at the National Academy for the Performing Arts (NAPA) in Trinidad last December, her first full-length concert in her home country. “I was so proud of my little island – because of the talent. You couldn’t ask for better. It was the greatest highlight of my year, and I will always remember it. My only regret was we couldn’t go for longer!”

This year looks to be a bumper one for the star. Her latest album is set for launch on 25 September, 2012. Then, in November – previews beginning on the 6th, with a premiere in December – she stars in a West End adaptation of the hit Hollywood film The Bodyguard. She plays Rachel Marron, the role Whitney Houston made famous. Houston’s impact on Headley was palpable after Houston’s death in February.

“I can’t even begin to fathom the weight of that right now. It weighed on me before, but now the challenge is even greater,” Headley said soon after news of Houston’s tragic passing broke. “There is and never will be a voice or gift like Whitney Houston’s. From the first time I heard her I knew I wanted to sing. As a child, I sat and listened to every song and knew every riff of Whitney’s. I actually remember where I was the first time I heard those first a cappella bars of ‘I Will Always Love You’.”

Headley’s own talent, discipline and drive will ensure she shines as brightly as she always has. But these days, she’s also concerned with helping as many other lights shine as possible, through work on causes close to her heart. For the 2011 Home concert in Trinidad & Tobago, she worked with British Gas to raise funds for the United Way. In Chicago, she and her husband are part of a scholarship school for inner-city kids.

“There’s something to be said for changing a child’s perception of who they are and can be,” she says. “When I was down in Trinidad, there was something in the kids’ eyes that I hadn’t seen before. It was like they were saying, ‘You did it, and we can do this too!’ So I want to find how we help them realise that, and get them ready. So we’re starting to look at it and talk to people to hopefully start something next year.”

Might Trinidad & Tobago ever see Heather Headley singing soca, or at Soca Monarch? “Oh gosh, no,” she says laughing. “I am not that good!”

She is interested in doing collaborations with artists from Trinidad & Tobago, however. “I think Destra’s got a great, great voice, and it would be fun at some point to just sit down and figure it out. That’s the beauty with us in the island…We listen to everything, so there are these Destras of the world who can sing calypso – unlike me – and then sing a Whitney Houston song and whatever else she wants to sing. And I’m really proud of all that.”

And how about the Tony-Grammy-Oscar trifecta? “Maybe I set my sights too high,” she says, “but then the other day I was saying, ‘God, I’ve got to get this Oscar thing and the Emmy…’ I never thought I’d have one, or even two!”

At 37, for this grounded and infinitely talented performer, anything is possible. And her birthplace, like her mother, will always be cheering her on.

Heather Headley’s honours


  • 2000 Tony Award for Best Actress in a Musical (Aida);
  • 2000 Drama Desk Award for Outstanding Actress in a Musical (Aida);
  • 2000 Sarah Siddons Award for Work in Chicago theatre;
  • 2003 Soul Train Lady of Soul Awards for Best R&B/Soul or Rap New Artist (“He Is”) and Best R&B/Soul Album of the Year – Solo (This Is Who I Am)
  • 2010 Grammy Award for Best Contemporary R&B Gospel Album (Audience of One)
Also named as one of:
  • People Magazine’s “50 Most Beautiful People”;
  • Essence Magazine’s “30 Women To Watch”.
Also nominated for: 
  • 2003 Billboard Music Award for R&B/Hip-Hop New Artist of the Year;
  • 2003 NAACP Image Awards for Outstanding New Artist and Outstanding Female Artist;
  • 2003 Soul Train Music Award for Best R&B/Soul or Rap New Artist (“He Is”);
  • 2004 Grammy Award for Best New Artist and Best Female R&B Vocal Performance (“I Wish I Wasn’t”);
  • 2006 BET J/Centric for Cool Like That Award;
  • 2010 Grammy Award for Best Gospel Performance (“Jesus Is Love”);
  • 2010 Dove Awards for Female Vocalist of the Year, Contemporary Gospel Album of the Year (Audience of One), and Event Album of the Year for “Oh Happy Day”

Heather Headley’s albums & recordings

Also credited on: 
  • The Lion King on Broadway Cast Recording (1997);
  • Return to Pride Rock (1998);
  • Do Re Mi (1999 Encores! production with Nathan Lane, Randy Graff, and Brian Stokes Mitchell);
  • Aida Original Broadway Cast Recording (1999);
  • Golden Dreams (2001);
  • Dreamgirls in Concert (2002 with Audra McDonald and Lillias White);
  • Oh Happy Day (2009, with Al Green)

Details of The Bodyguard’s West End run


• 6 November 2012 – 27 April, 2013 (first booking period) at the Adelphi Theatre, Strand, London WC2.
• Shows Monday – Saturday at 7.30pm; Wednesday and Saturday matinees at 3pm


• Previews: £20 – £57.50 including £1 theatre restoration levy
• Post-premiere: £20 – £67.50 including £1 theatre restoration levy
• Day seats: A limited number of £25 day seats will go on sale from the Box Office at 10am on the day of the performance
No booking fee for tickets purchased directly from the Adelphi Theatre (+44 844579 0094) or The Bodyguard website.

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