A modern-day poetic outlaw, Waylon Payne earned positive notices for his 2003 debut album The Drifter but he wasn't able to immediately capitalize on its good reviews. Instead, he dabbled in acting -- he appeared in the 2005 Johnny Cash biopic Walk the Line -- as he struggled with personal problems, eventually re-emerging in 2020 to widespread acclaim for his song cycle Blue Eyes, The Harlot, The Queer, The Pusher & Me.

Waylon Payne is the son of Jody Payne, a guitarist in Willie Nelson's band, and country singer Sammi Smith; he was named after his godfather, Waylon Jennings. He began his career writing songs and playing with other musicians. Notably, he placed "Elvis" and "Sing 'Til I Stop Crying" on Pat Green's album Wave on Wave in 2003, also singing and playing guitar on the disc. He had already finished recording his own album, The Drifter, without a label deal and was playing with Nelson in New York when Green suggested he play the record for Green's label, Republic/Universal. Payne was signed to the label, which released The Drifter on June 22, 2004. It attracted critical praise and was tapped by other artists for material. Django Walker put "Her (She's Gone)" on his album Six Trips Around the World, and "The Bottom" was covered by both Keith Gattis, producer of The Drifter (on Big City Blues, for which Payne sang background vocals), and Charlie Robison (on Good Times). Payne, also an aspiring actor, was cast in the role of Jerry Lee Lewis in the Johnny Cash biopic Walk the Line, which opened in 2005. Payne's appearance on the soundtrack album allowed him to share the Grammy Award won by the disc. He was next cast in the starring role of Hank Garland in the 2006 biopic Crazy. CBuJ Entertainment reissued The Drifter on March 11, 2008.

Payne spent the 2010s working behind the scenes as a songwriter and supporting musician. Additionally, he spent some time battling addiction, getting clean by the end of the decade. He re-emerged as a performing artist in 2020 with the acclaimed album Blue Eyes, The Harlot, The Queer, The Pusher & Me.