Toby Keith’s “Should’ve Been A Cowboy” Named Best Country Song Of The ’90s

Toby Keith’s “Should’ve Been A Cowboy” topped Ranker’s fan-voted list as the best country song of the 1990s, beating Garth Brooks’ “Friends in Low Places” for the number one spot.

The track, Keith’s debut single released in February 1993, reached number one on Billboard’s Hot Country Songs chart on June 5, 1993, staying there for two weeks.

Keith called the song “the foundation for me of everything” during a 2018 interview, noting he performed it at every show throughout his career despite having 15-20 other number one hits he didn’t always play.

The song launched Keith’s legendary career, which eventually earned him posthumous induction into the Country Music Hall of Fame in October 2024, eight months after his death from stomach cancer in February 2024. 

Categorised in: Country Music News

This post was written by Cheryl Johnstone