Cheyenne Jackson made his Broadway debut understudying both male leads in the Tony Award-winning musical Thoroughly Modern Millie. He later served as the standby for the character of Radames in Aida, then originated the role of Matthew in the off-Broadway production of Altar Boyz. In 2005, he originated his first Broadway leading role in the musical tribute to Elvis Presley, All Shook Up.
His performance as Chad earned him much critical praise, the Theatre World Award, as well as nominations from the Drama League and Outer Critics Circle Awards for Outstanding Lead Actor. In 2006, he starred off-Broadway in playwright Nicky Silver's The Agony and The Agony with Victoria Clark. In June 2007, less than a week before the scheduled opening night, Cheyenne Jackson assumed the lead role of Sonny on Broadway in Xanadu.
He replaced actor James Carpinello who had been injured during rehearsal. Previous workshop productions of the musical starred Jackson and Jane Krakowski. However, both Cheyenne Jackson and Krakowski opted out of the initial Broadway run, citing schedule conflicts.
His performance as Sonny would go on to earn him nominations from the Drama League and Drama Desk for Outstanding Lead Actor. Xanadu had several Tony Award nominations including "Best New Musical" for which Cheyenne Jackson and the cast performed on the 62nd Tony Awards show.
In 2008, Jackson re-teamed with Jane Krakowski and Sean Hayes in the New York City Center's Encores! production of Damn Yankees. He returned to Encores! in 2009, playing Woody Mahoney in the staged concert of Finian's Rainbow which was praised by critics. Cheyenne Jackson also starred in the development workshop of Book of Mormon by Trey Parker, Matt Stone, and Robert Lopez (who co-wrote the music for Avenue Q).
He has guest starred on television series including; Lipstick Jungle, Life on Mars, Ugly Betty, and has a recurring role on the award winning NBC series, 30 Rock. On March 15, 2010 Cheyenne Jackson made his guest-starring debut on the long-running NBC series, Law & Order in an episode entitled Innocence. Cheyenne Jackson filmed a sitcom pilot for ABC-TV called It Takes A Village co-starring Christopher Sieber and Leah Remini, which was not picked up for the Fall 2010 season.
Cheyenne Jackson has starred in several notable webisode series including; "Cubby Bernstein" opposite Nathan Lane, "Legally Brown" with Allison Janney , and "The [title of show] Show" from the meta-fictional Broadway musical [Title of Show].
In March 2009, Jackson made his nightclub debut at Feinstein's at Lowes Regency with a sold out one man show titled "Back to the Start". He later teamed up with Michael Feinstein to create a nightclub act titled "The Power of Two". The show was praised by the New York Times, Variety, and the New York Daily News among others. A CD of the show was released on November 3, 2009.
In October 2009 Cheyenne Jackson opened on Broadway to positive critical reviews reprising the role of Woody Mahoney in the Broadway revival of the 1947 musical Finian's Rainbow at the St. James Theatre, costarring with Jim Norton and Kate Baldwin. The Wall Street Journal raved, "The way that [Kate Baldwin] and Cheyenne Jackson sing "Old Devil Moon" is the stuff best-selling cast albums are made of."Despite the rave reviews and great word of mouth, the show closed on Broadway on January 17, 2010.
Jackson was a featured performer on the New York Daily News float and telecast of NBC's coverage of the 83rd Annual Macy's Thanksgiving Day Parade singing "Play To Win", composed by Michael Feinstein and William Schermerhorn. Along with the company of Finian's Rainbow, he recorded the Broadway revival cast album in early December 2009, with a release date of February 2, 2010.
Cheyenne Jackson will be featured in a prominent guest role during Season 8 of Curb Your Enthusiasm. His character "Terry" will be Larry David & Wanda Sykes personal trainer.
Cheyenne Jackson was recently cast in Glee to play Dustin Goolsby, the coach of "Vocal Adrenaline," the main rival of "New Directions".
The Power of Two, a concert reuniting Cheyenne Jackson and cabaret veteran Michael Feinstein, was presented to rave reviews at Carnegie Hall on October 29, 2010.
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