Toby Keith’s ‘Should’ve Been A Cowboy Tour XXV’ Marks Debut’s Silver Anniversary

The song that started it all comes full circle in 2018 with the Toby Keith Should’ve Been A Cowboy Tour XXV presented by Ford F-Series. Released to radio 25 years ago this month and went on to be the most played country song of that decade, “Should’ve Been A Cowboy” kicked off a multi-platinum career that – appropriately since it was written solely by Toby – eventually led to his induction in the Songwriters Hall of Fame (2015).

The tour opens April 6 in Salt Lake City and, to-date, travels throughout North America. Like all his recent tours, the trek is presented by Ford F-Series and promises a full complement of Toby’s too-many-for-the-setlist hits. Sure to be among them, of course, is “Should’ve Been A Cowboy.”

Another song he wrote, “I Love This Bar,” was recently honored by BMI for more than 4 million performances on commercial radio stations. And it all began more than 25 years ago with an off-hand comment.

BMI’s David Preston,
Scotty Emerick, and Toby Keith

“Cowboy” Stats

Writer: Toby Keith

Produced by Nelson Larkin and Harold Shedd

Released February 12, 1993

Debut album Toby Keith released April 20, 1993

Two-week Billboard No. 1 June 5 & 12

BMI Country Award Winner (1994)

Nearly 7 million BMI radio performances

Most played country song of the 1990s

More than 200 million views/plays across streaming services

History behind “Cowboy”

Toby was at a bar with some hunting buddies when one asked a woman to dance. She declined. A cowboy approached the same woman and his dance request was accepted, prompting Toby to say, “John, you should’ve been a cowboy.” That night, back at his hotel, he wrote the song in about 20 minutes, holed up in the bathroom as his roommate slept. His inspiration included the TV series Gunsmoke.

While sound-checking with the song as a member of a house band, Toby was approached by the late Chris LeDoux, who asked to record the song. He then informed him he’d just been signed to Mercury and the song would be his first single.

“Should’ve Been A Cowboy” has carried as far as Toby’s performances at forward operating bases in war zones during his USO Tours, inclusion in the video game Rock Band, and to a stage in Saudi Arabia, where he was the nation’s first western performer.

This legendary hit had me reeled in from day one and kept me hanging on over the years. Have lost count of how many shows I have seen, needless to say it has been many. To get all the current dates and more that will be announced “saddle up” and get over to

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