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.. "Honky Tonk Man", a remake of the Johnny Horton song, and "Guitars, Cadillacs" were hit singles.

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His third LP, Buenas Noches from a Lonely Room, included his first No. 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".

1, a duet with his musical idol, Buck Owens, on "Streets of Bakersfield". 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. Johnny Cash once cited Yoakam as his favorite country singer.

Chris Isaak called him as good a songwriter that ever put a pen to paper.

Dwight David Yoakam (born October 23, 1956) is an American singer-songwriter, actor, and film director, most famous for his pioneering country music.

Popular since the early 1980s, he has recorded more than twenty one albums and compilations, charted more than thirty singles on the Billboard Hot Country Songs charts, and sold more than 25 million records.

He has recorded five Billboard #1 albums, twelve gold albums, and nine platinum albums, including the triple platinum This Time. During his high school years, he excelled in both music and drama, regularly securing the lead role in school plays, such as "Charlie" in a stage version of Flowers for Algernon, honing his skills under the guidance of teacher-mentors Jerry Mc Afee (music) and Charles Lewis (drama).In addition to his many achievements in the performing arts, he is also the most frequent musical guest in the history of The Tonight Show. Outside of school, he sang and played guitar with local garage bands, and entertained his friends and classmates with his impersonations, such as Richard Nixon, who, at the time, was heavily embroiled in the Watergate controversy.Yoakam briefly attended Ohio State University, but dropped out and moved to Los Angeles in 1977 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.