Tag Archives: Should’ve Been a Cowboy

Toby Keith Celebrates 25 Years of No. 1 Debut Single, “Should’ve Been a Cowboy”

Toby Keith Celebrates 25 Years of No. 1 Debut Single, “Should’ve Been a Cowboy”

Toby Keith’s 1993 debut single, “Should’ve Been a Cowboy,” helped ignite a career that has seen the Oklahoma native win multiple CMA Awards and ACM Awards, earn 20 No. 1 singles and sell more than 40 million albums worldwide. To celebrate the 25th anniversary of Toby’s breakthrough song and self-titled debut album—which also included Top…

Toby Keith Announces “Should’ve Been a Cowboy Tour XXV”

Toby Keith Announces “Should’ve Been a Cowboy Tour XXV”

Toby Keith will celebrate the 25th anniversary of the release of his No. 1 song, “Should’ve Been a Cowboy,” with a tour of the same name. The tune, which was penned by Toby, hit the top of the Billboard chart for two weeks in June 1993. Toby’s tour will kick off on April 6 in…

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