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Dwight Yoakum was born in Pikeville, Kentucky, and raised in Columbus, Ohio, growing up with his mother and step-father, who had a white-collar job in the automotive industry. He graduated from Columbus's Northland High School on June 9, 1974. During his high school years, he excelled in both music and drama, regularly securing the lead role in school plays, such as Charlie in the stage version of Flowers for Algernon. Outside of school, Dwight Yoakum sang and played guitar with local garage bands, and frequently entertained his friends and classmates as an amateur comedian, impersonating politicians and other celebrities, such as Richard Nixon, who, at that time, was heavily embroiled in the Watergate controversy.

Dwight Yoakum briefly attended The Ohio State University, but dropped out and moved to Nashville in the late '70s with the intent of becoming a recording artist. When he began his career, Nashville was oriented towards pop Urban Cowboy music, and Yoakam's brand of Bakersfield honky tonk was not considered marketable. He began playing live in the Los Angeles area, performing with punk bands like Dead Kennedys, Butthole Surfers and X; and roots-rock bands The Blasters and Los Lobos.

Dwight Yoakum's recording debut was on the independent album A Town South of Bakersfield, planned and produced by Pete Anderson, in 1984 (1984 in music). His debut LP was 1986's Guitars, Cadillacs, Etc., Etc. and it instantly launched his career (1986 in music). "Honky Tonk Man" (Johnny Horton) 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, a duet with Buck Owens, "Streets of Bakersfield". 1990's (1990 in music) If There Was a Way was another best-seller.

Dwight Yoakum's song Readin', Rightin', Route 23 pays tribute to his childhood move from Kentucky, and is titled after a local expression describing the route that rural Kentuckians needed to take to find a job. (U.S. Highway 23 runs north from Kentucky through Columbus and Toledo, and through the automotive centers of Michigan.)

Dwight Yoakum has also taken some acting roles, most notably as the abusive alcoholic Doyle in Billy Bob Thornton's Sling Blade (1996) and as a sociopathic killer in 2002's Panic Room. He has also appeared in Southern California live theater, combining his acting talents with the talents of director Peter Fonda.

Having diverged from pop-icon status in country-western fare, Dwight Yoakum is today more likely to be identified as having an older, more traditional style. But along with his bluegrass and honky-tonk roots, Yoakam has written or covered many Elvis Presley-style rockabilly songs, including his popular covers of Queen's "Crazy Little Thing Called Love" in 1999 and Presley's "Suspicious Minds." He even recorded a cover of the Clash's "Train In Vain" in 1997.