Toby Keith

Toby Keith’s Milestone Year Celebrates 25th Anniversary

Twenty-five years ago, an Oklahoma oil field worker, football player and part-time honky tonk singer and songwriter got his big break as one of three artists sent on a promotional tour by Mercury Records. Working harder than anyone and doing everything to find his path to success, Toby Keith defied expectations as his debut single “Should’ve Been A Cowboy” went to No. 1 that year. In 2018, a career stamped by determination and defiance landed Keith as BMI’s top country songwriter in terrestrial radio airplay. 

As Keith closes another memorable year marked by celebrations of his auspicious launch – which are ongoing with the just released vinyl reissue of his re-mastered debut album – he also continues to create culturally relevant music that moves the needle. Highlights:

  • * In December, BMI celebrated 25 years of “Should’ve Been A Cowboy” with an event punctuated by a surprise appearance by NFL great Terry Bradshaw. BMI executive Jody Williams revealed that with more than 91 million commercial radio performances worldwide, Toby Keith is the organizations’ top country songwriter in terrestrial country radio. Additionally, “Should’ve Been A Cowboy” alone has received seven million airplay spins, which equates to 42 years of back-to-back consecutive airplay.
  • * December also brought recognition as Spotify’s Hot Country Playlist Cover Story, a Grand Ole Opryperformance (Dec. 7) and a performance at the Nashville Symphony Ball (Dec. 8), where Keith received the prestigious Harmony Award.
  • * The re-mastered, re-named version of Keith’s self-titled debut album Toby Keith – Should’ve Been A Cowboy [25th Anniversary Edition] hit stores and digital platforms November 30. As mentioned earlier, the vinyl version landed December 14. Beyond the debut single and three other smash singles – “He Ain’t Worth Missing,” “A Little Less Talk And A Lot More Action,” “Wish I Didn’t Know Now” – the release also includes three vault tracks. 
  • * A new video for “Should’ve Been A Cowboy” featuring scenes from live Toby Keith performances including his many USO Tours was released on Veterans Day weekend. Re-mastered videos for the original “Should’ve Been A Cowboy,” “A Little Less Talk And A Lot More Action,” “He Ain’t Worth Missing” and “Wish I Didn’t Know Now” were also released to support the album launch. 
  • * A round of golf in May led to a song that may ultimately stand with the best work of Keith’s career. Like his first single, “Should’ve Been A Cowboy” and many others, “Don’t Let The Old Man In” was born of a casual one-liner, but this one was delivered by film icon Clint Eastwood. Keith wrote the song by himself and sent it to Eastwood, who has included it over the closing credits of his new film The Mule. The song is also featured in the trailer and commercials. 
  • * The 15th AnnualToby Keith & Friends Golf Classic raised more than $1,090,000 to continue the work of OK Kids Korral, which provides a cost-free home to children and families seeking treatment at area hospitals. Performers included Mac McAnally, Paul Overstreet, Jamey Johnson and Keith. Two hunting trips with Navy SEALS were the top auction items at $55,000 each. Attendees included Olympic gold medalists Mike Eruzione and Bart Conner, basketball great Nancy Lieberman, NFL legends Ray Childress and Walt Garrison, and actor/musician/poet Red Steagall. 
  • * The Toby Keith Should’ve Been A Cowboy Tour XXV presented by Ford F-Series packed venues across North America from April to October.  
  • * Finally, asked this year what he might say to the younger version of himself on the brink of his first recording session, Keith replied: “One thing you can’t tell him, because they won’t let you, is, ‘Be more yourself.’ I fought with my first label until I got sick of it, put my foot down and risked my whole career. So I think maybe I should have done that sooner, but it’s overwhelming at that point. You’re walking into a world famous room full of triple scale musicians and legendary producers. How do you start laying down the law and not look like an asshole? You still gotta be someone they want to work with.”

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