Cheyenne grew up on the rural Idaho-Washington border, and later honed his acting craft in Seattle's thriving theatre community. In June 2002, he moved to New York City, and within a few weeks 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 "Disney's Aida" and then originated the role of "Matthew" in the hit off-Broadway production of "Altar Boyz".

His big break came in the fall of 2004 when Miramax producers asked him to leave "Altar Boyz", and originate his first Broadway leading role in "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 for Outstanding Lead Actor.

In 2005, Jackson made his film debut in the taut and edgy film "Curiosity" - which was the surprise hit of the Palm Springs International Short-Film Festival.

In 2006, Cheyenne portrayed "Mark Bingham" in Universal Pictures Academy Award nominated film, "United 93", directed by British film maker Paul Greengrass (Bloody Sunday, and The Bourne Supremacy). He also starred Off-Broadway in playwright Nicky Silver's "The Agony and The Agony" with Victoria Clark.

In 2007, Cheyenne returned to Broadway as Sonny Malone in the critical and box office hit "Xanadu".His performance earned nominations from the Drama League and Drama Desk for Outstanding Lead Actor. Additionally, he portrayed "Sebastian Kinglare" for the Sony /Lifetime Television pilot "Family Practice" and completed production on the feature film "Hysteria"

In 2008, Cheyenne starred as Joe Hardy in the New York City Center production of Damn Yankees, opposite Jane Krakowski and Sean Hayes. He also guest starred on NBC's "Lipstick Jungle" and recorded the cast album of Red Eye of Love.

Cheyenne has studied acting with Larry Moss and voice with Liz Caplan. He is also a proud member of the gospel choir Broadway Inspirational Voices.

When not performing, Jackson volunteers his time to a host of charities, including amfAR, the ASPCA, Broadway Cares/Equity Fights AIDS, and theater workshops for inner-city youth. A passionate animal lover, he shares his Manhattan home with Zora, a gorgeous Lab/Rottweiler mix rescued from a Harlem animal shelter.