The title track 'In My Mind' (written and produced by India.Arie collaborator Shannon Sanders) was released as the first single and its music video was directed by Diane Martel. Under BMG North America chairman/CEO Clive Davis for the first time, Headley released her second album In My Mind in January 2006. Her second album, In My Mind (2006) was delayed due to the various executive shake-ups associated with RCA parent BMG's merger with Sony. The work on this album earned her a Grammy Award nomination for Best Female R&B Vocal Performance and for Best New Artist making her the first Tony Award winner to be nominated for this award. Although its first single, 'He Is', was not very successful, the second single, 'I Wish I Wasn't', achieved moderate success. Headley released her debut album, This Is Who I Am, in October 2002 with RCA Records.

She also voices of the part of Fikiri as Makini's Mother in The Lion Guard. ДЇrom 2017, Headley is co-starring in Spike Lee's Netflix reboot of She's Gotta Have It as Dr Jamison. On May 10, 2016, Headley assumed the role of Shug Avery from Jennifer Hudson in the recent Broadway revival of The Color Purple, which closed on Januat the Bernard B. Heather joined the Andrea Bocelli UK Tour playing Glasgow Hydro on November 23 and at the Leeds First Direct Arena on November 24, 2013. She was nominated for an Olivier Award and a What's On Stage Award for this performance. On March 12, 2009, Headley sang 'I Wish' on The Tonight Show with Jay Leno.ДЇrom November 2012 until August 2013, Headley played the role of Rachel Marron, in the musical adaptation of Whitney Houston's 1992 movie, The Bodyguard at London's Adelphi Theatre. Headley sang ' My Country, 'Tis of Thee' (also known as 'America') with Josh Groban on January 18, 2009, during the We Are One: The Obama Inaugural Celebration at the Lincoln Memorial. They performed Vivo Per Lei and The Prayer. On July 5, 2007, Headley made a guest appearance for Andrea Bocelli's Vivere Live in Tuscany concert in Lajatico, Italy. In the autumn of 2006, Heather performed Hal David and Burt Bacharach's song ' I'll Never Fall In Love Again', from the 1968 musical Promises, Promises, for 'The Kennedy Center Presents: The 2006 Mark Twain Prize', honoring playwright Neil Simon. She starred in an Actors' Fund of America benefit concert version of the musical Dreamgirls alongside McDonald and Lillias White in 2001. In 1999, she appeared in the Encores! staged concert production of Do Re Mi, with Nathan Lane, Randy Graff, and Brian Stokes Mitchell. 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 2000. Her breakthrough came the following year when she originated the role of Nala in the Broadway musical The Lion King. Headley's stage career began in 1996 when she was cast as a member of the ensemble in the original Toronto production of the musical Ragtime where she was an understudy for Audra McDonald in the role of Sarah. She is featured in their song 'How Great Is The Love' and 'All Glory'. Headley regularly performs with Vertical Church Band, the worship team from Harvest Bible Chapel. In April 2019, the couple welcomed a third child, a daughter. Headley had her second son Jordan Chase August 18, 2014.

On December 1, 2009, they welcomed their first child John David. In 2003, Headley married Brian Musso, an investment advisor who briefly played for the New York Jets. After graduating from Northrop High School, Headley attended Northwestern University from 1993 to 1996, to study communications and musical theatre until the last day of her junior year, when she made the decision to become a part of the musical Ragtime and drop out of school.

Headley attended Northrop High School, and was a member of their resident show choir, Charisma, and starred as Fanny Brice in the school's production of Funny Girl. In 1989, she moved to Fort Wayne, Indiana, in the United States at the age of fifteen with her mother and brother Eric Junior when her father was offered a job as pastor of McKee Street Church of God with headquarters in Anderson, Indiana. Headley was born in Trinidad, the daughter of Hannah and Eric Headley (Barbadian).

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