Toby Keith tells the story behind ‘Should’ve Been a Cowboy’ before celebrating the 25th anniversary of the hit at Coastal Country Jam

Twenty-five years ago country singer-songwriter Toby Keith was on a hunting trip with about two dozen buddies when the crew, still clad in their camouflage clothing, walked into bar in Dodge City, Kansas, the setting for the award-winning television series “Gunsmoke.”

One of the guys in the group, a highway patrolman, decided to walk up to a cowgirl in the bar and ask her to dance.

He was promptly shot down.

“She guns him down and everyone makes fun of the poor guy and he comes back to the table and a young guy, about half his age, swoops in and takes her to the floor,” Keith recalled during a recent phone interview. “One of them turned and said ‘John, you should’ve been a cowboy.’ I thought, well, I have to write that.”

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Country star Toby Keith will headline Costal Country Jam at Huntington State Beach on Sunday, April 8. (Photo by Greg Watermann)

Keith headed back to his hotel room and wrote his first single and No. 1 hit, “Should’ve Been a Cowboy” in about 20 minutes. The single was released Feb. 12, 1993, and his self-titled debut album came out on April 20, 1993.

To commemorate the 25th anniversary of the song that started Keith’s successful music career, he’s currently out on the Should’ve Been a Cowboy Tour XXV, which comes to Huntington State Beach on Sunday, April 8, as Keith & Co. help kick off the first of three Coastal Country Jam festivals on the beach. The show also features Granger Smith, Frankie Ballard, Jerrod Niemann, Jobe Fortner, Alexandria Corn and Christie Huff.

“Should’ve Been a Cowboy” was one of the most played country songs of the ’90s and helped earn Keith his spot in the Songwriters Hall of Fame, where he was inducted in 2015 by “The Late Show” host Stephen Colbert. Though he’s had dozens of hits since then including “As Good As I Once Was,” “Who’s Your Daddy?,” “How Do You Like Me Now?,” “Courtesy of the Red, White and Blue,” “Beer for my Horses,” “Red Solo Cup,” “I Love This Bar,” “A Little Too Late” and more, he never leaves “Should’ve Been a Cowboy” out of his live performances. Not only does the song serve as the memory of a pivotal moment in Keith’s career, his fans pretty much demand that he play it.

He remembers Mercury Records VP of promotions Anne Weaver anxiously waiting for the numbers to come back in from the radio stations to see if the single was going to move or if they’d have to can Keith’s debut record. They cut it close, waiting for three or four stations to report back. Keith said he was sweating bullets, but when the positive results came in, they knew they had a hit.

“She said to me, ‘I’m going to be real honest with you, it’s been at 28 for two or three weeks in a row, and if it stays at 28, we’re going to lose this record’,” Keith recalled. “I said ‘Really?’ Yup. Sure enough, those three or four stations came in and the thing just took off and soared to number one, but I remember what it was like, sitting there on the breaking point.”

The first time Keith and his band heard the song on the radio they were traveling from a gig in Nashville to a date in Louisville, Kentucky and once they hit Bowling Green, the local DJ cued up the song.

“Everyone just shut up and when it came on, we cranked it up,” he said. “It’s such an important piece of the puzzle that I don’t think I’ve ever done or will ever do a show without playing it. When your first one is that big, it gives you a little breathing room to feel your way around whereas there’s so many people that are really talented that lost their opportunity to have success because their first couple of songs weren’t hits.”

Coastal Country Jam

With: Toby Keith, Granger Smith, Frankie Ballard, Jerrod Niemann, Alexandria Corn, Christie Huff and Jobe Fortner

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