Yoakam’s recording debut was on the compilation album A Town South of Bakersfield, which was a collection of ‘New Country’ artists who were based in Los Angeles. He released an E.P. on independent label Oak Records; this was later re-released, with several additional tracks, as his major-label debut LP, 1986’s Guitars, Cadillacs, Etc., Etc.. It launched his career. ‘Honky Tonk Man’, a remake of the Johnny Horton song, and ‘Guitars, Cadillacs’ were hit singles. The follow-up LP, Hillbilly Deluxe, was just as successful. His third LP, Buenas Noches from a Lonely Room, included his first #1 single, a duet with his musical idol, Buck Owens, on ‘Streets of Bakersfield’. 1990’s If There Was a Way was another best-seller.
Along with his bluegrass and honky-tonk roots, Yoakam has written or covered many Elvis Presley-style rockabilly songs, including his covers of Queen’s ‘Crazy Little Thing Called Love’ in 1999 and Presley’s ‘Suspicious Minds’ in 1992. He recorded a cover of the Clash’s ‘Train in Vain’ in 1997, a cover of the Grateful Dead song ‘Truckin”, as well as Cheap Trick’s ‘I Want You to Want Me’. Yoakam has never been associated only with Country music; on many early tours, he played with Hardcore Punk bands like H_sker D_, and played many shows around Los Angeles with Roots/Punk/Rock & Roll acts. His middle-period-to-later records saw him branching out to different styles, covering Rock & Roll, Punk, 1960’s, Blues-based ‘Boogie’ like ZZ Top, and writing more adventurous songs like ‘A Thousand Miles From Nowhere’. In 2003, he provided background vocals on Warren Zevon’s last album The Wind.
In 2000, Yoakam released dwightyoakamacoustic.net, an album featuring solo acoustic versions of many of his hits. He then left his major label and started his own label. His most recent album of new material is 2005’s Blame the Vain, on New West Records. Yoakam also released an album dedicated to Buck Owens, Dwight Sings Buck, on October 23, 2007. Yoakam is currently working on a new original album, expected in 2011. His duet with Michelle Branch, ‘The Long Goodbye’ is expected to be released as a single at the beginning of 2011 as well.