Crenshaw's music has roots in classic soul music, British Invasion song craft, with influences from Burt Bacharach and Buddy Holly. Crenshaw is a noted guitarist who uses offbeat chord progressions and concise solos. He is best known for eponymous first album included the US hit "Someday, Someway".

The great alt-country band Uncle Tupelo played its last concert on May 1, 1994, at Mississippi Nights in St. Louis, Missouri. By the time of this show, Jeff Tweedy and Jay Farrar were already not getting along well. Soon after the performance, they would both go on to create other bands, with Farrar founding Son Volt and Tweedy forming Wilco, but on that night in May 1994, there was one last grasp at combined harmony and greatness. In the video below, Tweedy and Farrar trade off on the lead vocals, with drummer Mike Heidorn joining the band on the final song of the set, “Looking for a Way Out,” and also singing on the encore with Brian Henneman and the Bottle Rockets on Lynyrd Skynyrd’s “Gimme Three Steps.”

Uncle Tupelo at Jake's in Bloomington, Indiana 1992. Tracks include: Satan, Your Kingdom Must Com Down, No Depression, Watch Me Fall, Gun and many others.