Of Choctaw descent through his paternal grandmother and African-American through his grandfather,[6] Cherry is the fourth of five siblings.

[7] At 16, he enrolled in the High School of Performing Arts in New York in the same class as Jennifer Aniston and Chaz Bono.

[11] He began writing and recording his debut album, Desireless, in his bedroom studio on an acoustic guitar.

[11] According to manager Tommy Manzi, Cherry's perfectionism made him keep the recordings under wraps until the album was virtually complete.

[7] Cherry co-wrote and sang on "Wishing It Was" on Santana's 1999 album Supernatural,[7] as well as in films such as Wim Wenders' The Soul of a Man, Y tu mamá también, The Love of the Game, GO, Best Laid Plans, Holes, Billy Elliot and Over Her Dead Body.