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He gained prominence in 1988 when he became one of the few African Americans to head a notable nonprofit theater company as the artistic director of Atlanta's Alliance Theatre Company. During Leon's tenure, the company staged premieres of Pearl Cleage's Blues for an Alabama Sky, Alfred Uhry's The Last Night of Ballyhoo, and Elton John and Tim Rice's musical Aida, which went on to Broadway. The Alliance's endowment also rose from $1 to $5 million during his time there.
Leon resigned from the Alliance in 2000 to take on other projects. These included being the co-founder and artistic director of True Colors Theater Company, a group based in both Atlanta and Washington, D.C. He also took his talents to Broadway. In the spring of 2004 he directed a revival of Lorraine Hansberry's A Raisin in the Sun, starring Sean Combs, Phylicia Rashād and Audra McDonald in his Broadway debut. At the end of that year, he directed the Broadway premiere of August Wilson's Gem of the Ocean. In spring 2007, he directed August Wilson's Radio Golf. All three plays were nominated for Tony awards, and Leon was a Drama Desk Award nominee for A Raisin in the Sun. He also directed the television version of A Raisin in the Sun, which aired on ABC in February 2008. Leon was nominated for a Tony Award in 2010 for Best Director for his work on August Wilson's Fences, starring Denzel Washington and Viola Davis, earning them both nominations and wins for Best Performance for Male and Female in a Play.
Leon has also directed plays at the Cincinnati Playhouse in the Park, the Huntington Theater Company in Boston, the New York Shakespeare Festival, and the Goodman Theater in Chicago among many others.
In January 2012, he completed a Lifetime Original Lifetime Television remake of Steel Magnolias. Other projects include a staged adaptation of the 1967 film Guess Who's Coming to Dinner; and a musical inspired by the work of rapper Tupac Shakur.
Leon is a graduate of Clark Atlanta University. In addition to his directing experience, he has extensive acting experience on stage and in television and film. He made an appearance in the Hollywood Black Film Festival winner Big Ain't Bad, playing the role of Thomas Jordan, the Mayor of Atlanta. In 2004, People named him one of the "50 Most Beautiful People" of the year. In 2007, Leon was a recipient of the 2007 Georgia Arts and Entertainment Legacy Award for his contributions to Georgia's cultural legacy.
- 1991 Driving Miss Daisy
- 1991 Spirit of Atlanta
- 1991 Miss Evers' Boys
- 1992 So Long on Lonely Street
- 1992 Playland
- 1993 A Streetcar Named Desire
- 1993 Two Trains Running
- 1995 Blues for an Alabama Sky
- 1996 The Last Night of Ballyhoo
- 1998 Aida
- 2004 A Raisin in the Sun
- 2004 Gem of the Ocean
- 2007 Radio Golf
- 2010 Every Tongue Confess
- 2010 Fences
- 2011 The Mountaintop
- 2011 Stick Fly
- 2013 Holler If Ya Hear Me
- 2008 A Raisin in the Sun
- 2009 Ghost Whisperer Episode: "Excessive Forces"
- 2010 Private Practice Episode: "'Til Death Do Us Part"
- 2011 Private Practice Episode: "Heaven Can Wait"
- 2012 Steel Magnolias
- Brock, Wendell (January 2012). "Leon Takes the Lead". Jezebel Magazine. p. 48. "'It doesn't get better than that...' says the Tallahassee, Fla., native who turns 56 in February."
- Playbill News: PLAYBILL.COM'S BRIEF ENCOUNTER with Kenny Leon
- "Kenny Leon - Real Life Defined on Stage", Global Community Communications Alliance.
- Kenny Leon's True Colors Theatre Company.
- Simi Horwitz, "Interview - Director Kenny Leon Juggles 'Dinner,' 'Steel Magnolias,' and Tupac Musical", Backstage, April 11, 2012.
- "Honoree Kenny Leon".