On this date in 1993, an Oklahoma native released his debut country single, “Should’ve Been a Cowboy,” a song that was a modest crossover hit as well as a massive smash on country radio. It topped the charts and ultimately netted over three million spins, making it the most-played country song of the ‘90s. Do you know who sang it? ANSWER: Toby Keith.
By Carena Liptak
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