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What awards has Heather Headley won? Heather Headley has won the Outstanding Actress in a Musical award at the Drama Desk Awards for her performance in Aida. Additionally, she received the Tony ...

Outstanding Actress in a Musical: Heather Headley was nominated but did not win. 2000 Tony Awards Best Performance by an Actress in a Leading Role in a Musical: Heather Headley won.

"I think my Helen craves what Heather has," Headley considers ... 2000 Tony for Best Actress in a Musical for the title role of Aida. "Singing on Sweet Magnolias this year was even more fun ...