After spending nearly a decade as the drummer with the seminal Minneapolis alt-country combo the Jayhawks, Tim O'Reagan stepped out from behind the kit to release a self-titled solo album in 2006, a breezy and sonically diverse set that proved O'Reagan was as good at singing, songwriting, and playing guitar as he was at keeping time. Tim O'Reagan got his start in music in Kansas City, where after several years of holding down the rhythm in R&B cover bands he formed the Leatherwoods with his friend Todd Newman. Boasting a catchy but easygoing pop sound with a bit of twang around the edges, the Leatherwoods moved to Minneapolis in search of a more sympathetic audience, and soon scored a deal with Twin/Tone Records, who released their album Topeka Oratorio in 1992.
While the Leatherwoods failed to gain the audience they deserved, O'Reagan's talents impressed Joe Henry enough that he was invited to join the noted songwriter's road band and played on two of his albums, Fireman's Wedding and Trampoline. In 1996, O'Reagan joined the Jayhawks after the departure of drummer Don Heffington, in time to go into the studio with them for the album Sound of Lies. By the time the Jayhawks recorded Rainy Day Music in 2003, O'Reagan was contributing to the band as a songwriter, guitarist, and backing vocalist as well as drumming, and when the group opted to take a sabbatical in 2005, O'Reagan began work on a solo album. Recorded and produced by O'Reagan and featuring Gary Louris, Marc Perlman and Mark Olson from the Jayhawks, and former Son Volt bassist Jim Boquist, Tim O'Reagan was released by Lost Highway on June 27, 2006.