Robert Lee Castleman grew up in various locations as the son of a career military man. He worked in a guitar shop and played in bars and folk clubs before moving to Nashville to become a songwriter, though he supported himself as a trucker. His song "Sneakin' Around" was used as the title track for a 1991 duet album by Chet Atkins and Jerry Reed, and he played rhythm guitar on Atkins' 1994 album Read My Licks. He also played behind Suzy Bogguss and Eric Johnson before attracting the attention of Alison Krauss through her husband, his friend Pat Bergeson. Krauss used his song "Forget About It" as the title track on her 1999 album and arranged an audition with her label, Rounder Records, which signed Castleman and released his debut album, Crazy as Me, in August 2000.