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Yoakam's honky tonk style was not the 'in' thing in country music at the time, so he had trouble finding kindred spirits. It wasn't until he had been in Nashville for months that he met guitarist Pete Anderson. The pair hit it off and soon moved to Los Angeles to find a more diverse audience. While in LA they played many nightclubs. They rounded the country music club circuit first, but then branched out into nightclubs that also featured punk and pos-punk bands like the Dead Kennedys and Los Lobos. Yoakam had common influences with the punk bands he followed in the LA clubs and audiences could hear the similarities. The fans that followed Yoakam soon earned the name of cow-punks. The success of Yoakam's club career prompted him to move on to bigger and better things.

Yoakam's decision to take his career to the next level resulted in the release of an independent EP titled A Town South of Bakersfield. The 1984 release was well received in the industry and was played often on LA college and alternative radio stations. The single also helped him to land a contract with Reprise Records. Two years later a full-length album called Guitars, Cadillacs, Etc., Etc. was released. It became an instant hit. Both rock and country critics praised Yoakam's efforts. Singles from the album began making their way onto radio stations across the country. A cover of Johnny Horton's 'Honky Tonk Man' made it to number three on the charts and helped boost the album to number four. It eventually went platinum in sales.

Fans were lined up for the release of his next album, Hillybilly Deluxe. It spawned four Top Ten hit singles'”'Little Sister', 'Little Ways', 'Please, Please Baby', and 'Always Late with Your Kisses'. His first number one hit came in 1988 with the single 'Streets of Bakersfield'. It was the first single off of his third album, Buenas Noches from a Lonely Room. In 1989 Yoakam's compilation album, Just Lookin' for a Hit, went gold. His 1990 release, If There Was a Way, was also a platinum success. Three years later, This Time was an even bigger success. Three number two singles, 'Ain't That Lonely Yet', 'A Thousand Miles from Nowhere', and 'Fast As You' all made it to number two on the charts.