When he began his career, Nashville was oriented toward pop “urban cowboy” music, and Yoakam’s brand of hip honky tonk music was not considered marketable.

Not making much headway in Nashville, Yoakam moved to Los Angeles and worked towards bringing his particular brand of new Honky Tonk or “Hillbilly” music (as he called it) forward into the 1980s. Writing all his own songs, and continuing to perform mostly outside traditional country music channels, he did many shows in rock and punk rock clubs around Los Angeles, playing with roots rock or punk rock acts like The Blasters (Yoakam scored a small video hit with his version of their song “Long White Cadillac”), Los Lobos, and X. This helped him diversify his audience beyond the typical country music fans, and his authentic, groundbreaking music is often credited with rock audiences accepting country music.

Yoakam’s recording debut was the self-financed EP Guitars, Cadillacs, Etc., Etc. on independent label Oak Records produced by lead-guitarist Pete Anderson; this was later re-released by Reprise Records, with several additional tracks, as his major-label debut LP, 1986’s Guitars, Cadillacs, Etc., Etc.. The record hit the market during a sea change in country music: the urban cowboy music was out of style, and neotraditional music based on classic styles, such as Yoakam’s honky-tonk inspired music, was now in demand. The LP was a breakout hit and spawned his first two hit singles: “Honky Tonk Man”, a remake of the Johnny Horton song, and the title track “Guitars, Cadillacs.” His stylish video “Honky Tonk Man” was the first country music video ever played on MTV. The follow-up LP, Hillbilly Deluxe, was just as successful. His third LP, Buenas Noches from a Lonely Room, included his first No. 1, a duet with his musical idol, Buck Owens, on “Streets of Bakersfield”. 1990’s If There Was a Way was another best-seller.

Yoakam’s song “Readin’, Rightin’, Route 23” pays tribute to his childhood move from Kentucky, and is named after a local expression describing the route that rural Kentuckians took to find a job outside of the coal mines. (U.S. Route 23 runs north from Kentucky through Columbus and Toledo, Ohio and through the automotive centers of Michigan.) Rather than the standard line that their elementary schools taught “the three Rs” of “Readin’, ‘Ritin’, and ‘Rithmetic”, Kentuckians used to say that the three Rs they learned were “Readin’, ‘Ritin’, and Route 23 North”.

Johnny Cash once cited Yoakam as his favorite country singer. Chris Isaak called him as good a songwriter as ever put a pen to paper. Time dubbed him “A Renaissance Man” and Vanity Fair declared that “Yoakam strides the divide between rock’s lust and country’s lament.” Along with his bluegrass and honky-tonk roots, he 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”. He has never been associated only with country music; on many early tours, he played with hardcore punk bands like Hüsker Dü, 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 the 21st century, Yoakam released dwightyoakamacoustic.net, an album featuring solo acoustic versions of many of his hits; left his major label and started his own label.[citation needed]

2005 saw the release of Yoakam’s well-reviewed album Blame the Vain, on New West Records. He also released an album dedicated to Buck Owens, Dwight Sings Buck, on October 23, 2007. His duet with Michelle Branch, a song titled “Long Goodbye”, was released as a free download on her official website in early 2011.

In July 2011, Yoakam re-signed with Warner Bros. Nashville and announced plans to release a new album. 3 Pears was released on September 18, 2012 with twelve new tracks. Produced by him, it includes a collaboration with Beck. 3 Pears was released to resounding critical acclaim and earned him the highest-charting debut of his career on the Billboard 200 and Billboard Country Albums charts. 3 Pears reached #1 on the Americana Radio chart on October 29, 2012 and went on to break the 2012 record for most weeks at #1 on Americana Radio. By the end of 2012, it was named on annual best of lists by NPR, Rolling Stone, American Songwriter, AOL’s The Boot, Entertainment Weekly, The Village Voice, and Rhapsody, and has been included in more critics’ “best of 2012” lists than any other artist in the country genre.

In June 2014, Rolling Stone ranked the song “Guitars, Cadillacs” #94 in their list of the 100 greatest country songs.

In February 2015, Yoakam announced a new studio album, titled Second Hand Heart and released on April 14. In 2016, he supported the album by performing at the C2C: Country to Country festival in Europe. He performed at the Americana Music Honors & Awards, announcing that he was working on a new album of all bluegrass songs. The album, titled Swimmin’ Pools, Movie Stars…, was released in September 2016.

At the 59th Grammys he introduced fellow Alt Country artist and friend Sturgill Simpson.

For more information visit dwightyoakam.com