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In June 2012, Jackson starred opposite Krysten Ritter in Neil La Bute's The Heart of The Matter produced by MCC Theater at the Lucille Lortel Theatre.In the 2012-2013 Broadway season, Jackson, Henry Winkler, Alicia Silverstone, Daniel Breaker, Jenni Barber and Ari Graynor starred in David West Read's play The Performers which started previews on October 23, 2012 at the Longacre Theatre.Jackson's first leading role on Broadway was in All Shook Up (2005), which earned him a Theatre World Award for "Outstanding Broadway Debut." Since then, on the New York stage, he has starred in The Agony & the Agony (2006), Xanadu (2007; Drama League, Drama Desk nominations), Damn Yankees (2008), Finian's Rainbow (2010; Drama Desk nomination), 8 (2011), The Heart of the Matter (2012) and The Performers (2013).He has also appeared in a number of films, including the 2006 Academy Award-nominated United 93, in which his portrayal of Mark Bingham earned him the Boston Society of Film Critics 2006 award for Best Ensemble Cast. Cheyenne starred on Broadway but became famous on "American Horror Story," where his character became the new owner of the haunted hotel. His credits include leading roles in Broadway musicals and other stage roles, as well as film and television roles, concert singing, and music recordings.In June 2007, less than a week before the scheduled opening night, Jackson assumed the lead role of Sonny on Broadway in Xanadu, replacing James Carpinello who had been injured during rehearsal.Previous workshop productions of the musical starred Jackson and Jane Krakowski.

Jackson made his Broadway debut understudying both male leads in the Tony Award-winning musical Thoroughly Modern Millie.In 2016, Jackson released his latest album, Renaissance, and a Vietnam veteran.His mother taught Jackson, his sister, and two brothers to sing and regularly played music by Joan Baez, Joni Mitchell, Bob Dylan and Elvis Presley at home. In Seattle, Jackson worked as an ad executive at a magazine and did some theater work on the side, earning his Equity card.In 2013, he starred in the HBO biopic of Liberace, Behind the Candelabra with Michael Douglas and Matt Damon.

Jackson plays Michael Minetti, who is hired by retiree Lily Harrison (Gena Rowlands) to give her private dance lessons at her home for six weeks.

James Theatre, costarring with Jim Norton and Kate Baldwin.