At age 17, he recorded an album of his songs with his parent's friend, famed Texas producer/pedal steel player Lloyd Maines, producing. While the album was never commercially released, Boston's Berklee School of Music offered Allen a full scholarship on the strength of the effort. After graduating from the school in 1991, Allen moved to Austin, where he played with the likes of Will Sexton, Kris McKay, Alejandro Escovedo, and Beaver Nelson.

Allen also played a few shows with Joe Ely, whose lead guitarist at the time was Ian Moore. When Moore left Ely to pursue a solo career, Allen followed him, doing several albums and national tours. In the late '90s Allen recorded Sweet Valentine, an album of his compositions, and released it independently. The album combined Allen's haunting vocals and strong piano work. For the effort, Allen hooked up with some of his old Berklee bandmates and recorded it in five days at My Generation Studios in Boston. Austin friends like Will Sexton and fiddler Richard Bowden guested on the release. ~ Erik Hage