Headley began playing the music of her native country at a young age, including calypso, reggae and soca. She moved to Fort Wayne, Indiana in the United States at the age of fifteen when her father was offered a job as pastor of McKee Street Church of God (in Anderson, Indiana).

After graduating from Northrop High School, Headley attended Northwestern University to study communications and musical theatre. In 1997, she played Nala in The Lion King, the Broadway musical. Headley's performance was well-received and she then originated the title role in the Broadway adaptation of Aida, earning the Tony Award for Best Actress in 1999.

Headley released her debut album, This Is Who I Am, in October 2002 on RCA Records. Although its first single, "He Is", was not very successful, the second single, "I Wish I Wasn't", achieved moderate success and earned her a Grammy Award nomination for Best Female R&B Vocal Performance. Headley was also nominated for Best New Artist.

On September 6, 2003, Headley married Brian Musso, formerly of the New York Jets. Her second album, In My Mind, was delayed due to the various executive shake-ups associated with RCA parent BMG's merger with Sony, and Headley joked that it should have been called Caught Up instead. Under BMG North America chairman/CEO Clive Davis for the first time, Headley released the album in January 2006. The title track was released as the first single; it was produced by India.Arie collaborator Shannon Sanders, and its music video was directed by Diane Martel. The song reached number-one on the U.S. Hot Dance Music/Club Play chart.

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Heather Headley (born October 5, 1974) is a Trinidadian R&B and soul singer, songwriter, record producer, and actress. She has won one Tony Award and one Grammy Award.