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R.I.P., Toby Keith: Country Music Superstar Behind 'Red Solo Cup' and 'Should've Been a Cowboy,' Dead at 62

'["Red Solo Cup"] is the stupidest song I ever heard in my life, but it's so stupid it's good,' Keith famously said of his biggest crossover hit

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Toby Keith at the 25th Anniversary Celebration of his 'Should've Been A Cowboy' held at BMI on December 5, 2018 in Nashville, TN

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Toby Keith, the country music singer responsible for taking an everyday object – namely, a red Solo cup – and turning it into a top-10 country hit as well as a top-20 hit on the Billboard Hot 100 – has died at the age of 62.

Per a statement on Keith’s official website this morning, he “passed peacefully last night...surrounded by his family.” His death was the result of a previously-announced battle against stomach cancer, one his family assured fans in their statement that he fought “with grace and courage.”

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Toby Keith at the Nashville Songwriter Awards 2023, held at the Ryman Auditorium on September 26, 2023 in Nashville, TN

Born Toby Keith Covel on July 8, 1961 in Clinton, Oklahoma, Keith’s musical education began in earnest as a result of his grandmother, who owned Billie Garner’s Supper Club in Fort Smith, Arkansas. Visiting her during the summers, he became fascinated by the musicians who performed there, getting his first guitar when he was only eight years old. It would be quite some time, however, before he pursued music in any serious fashion: he spent his high school years on the Moore High School football team in Moore, Oklahoma, and after graduation he picked up a job as a derrick hand in the oil fields, working his way up to operation manager.

It wasn’t until the age of 20 that Keith and some friends formed the Easy Money Band, splitting his time between the oil industry and playing music, and when the oil industry started to flag, he went back to football, playing semi-pro with the Oklahoma City Drillers while continuing with the band. Within a few years, however, he was able to focus solely on music, and by the early 1990s, Keith had made the move to Nashville, vowing to give up music as a career if he couldn’t pull a recording contract by the time he turned 30. Thankfully, he met his goal: he was signed to Mercury, and his first single, “Should’ve Been a Cowboy,” went to No. 1 on the US Country chart and even fought its way into the lower reaches of the Billboard Hot 100, hitting No. 93.

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It was in no way Keith’s only stop at the top spot on the Country chart: he ultimately ended up with 20 chart-topping hits, including the platinum-selling singles “How Do You Like Me Now?,” “I Wanna Talk About Me,” “Courtesy of the Red, White and Blue (The Angry American),” “I Love This Bar,” “American Soldier,” “Whiskey Girl,” “As Good As I Once Was,” “Made in America,” and his duet with Willie Nelson, “Beer for My Horses.”

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As noted, however, Keith’s success wasn’t limited solely to the country charts, In addition, he racked up a dozen top 10 albums - or 14 if you count his best-of collections - in the Billboard 200, four of which topped the chart. It took awhile for that success to make its way to the Hot 100 in a big way, however, but after securing a second Hot 100 entry with his duet with Sting on the latter’s “I’m So Happy I Can’t Stop Crying" (No. 84), he went on to amass 15 top 40 hits on the Billboard Hot 100. Of course, "Red Solo Cup” was his most substantial crossover hit, climbing to No. 15 and giving him his lone top-40 hit.

"It is the stupidest song I ever heard in my life," Keith told The Boot in 2014. "But it's so stupid it's good."

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In addition to his music, Keith also did a bit of acting, starring in the 2005 film Broken Bridges, playing a washed-up country musician alongside such notable co-stars as Burt Reynolds, Tess Harper, Kelly Preston, and Lindsey Haun (True Blood), plus a guest appearance by Willie Nelson as himself.

A few years later, Keith starred in a film adaptation of his hit duet with Nelson, Beer for My Horses, which – in addition to a terribly unsurprising appearance by Nelson, this time playing a character named Charlie – featured a disparate cast, including Rodney Carrington, Ted Nugent, Barry Corbin, Claire Forlani, Curtis Armstrong, Tom Skerritt,Mac Davis, Gina Gershon, David Allan Coe, Mel Tillis, and Cledus T. Judd.

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Keith’s politics started out somewhat unique for a country singer: in 2004, he described himself in an interview with the Boston Globe as “a conservative Democrat who is sometimes embarrassed for his party.” By the time of 2008 election, however, he had left the Democratic Party and re-registered as an independent, and although he pointedly showed support for President Obama on more than one occasion, he subsequently performed at Donald Trump’s 2017 pre-inaugural “Make America Great Again! Welcome Celebration” at the Lincoln Memorial in Washington, DC.

It's arguable, however, that what was more important to Keith than politics – indeed, something he felt transcended politics – was his support for those who served in the US military. As he told the American Forces Press Service, “My father was a soldier. He taught his kids to respect veterans. It’s that respect and the thank-you that we have a military that’s in place and ready to defend our nation; our freedom.”

Throughout his cancer battle, Keith kept his fans informed about his health and how his treatment was progressing. He made his post-diagnosis return to the stage on July 1, 2023 in Norman, Oklahoma, and as recently as December 2023 he performed a trio of shows at Dolby Live at Park MGM in Las Vegas, performing his final show on December 14.

The set list was as follows:

  1. Big Dog Daddy
  2. Made in America
  3. God Love Her
  4. I Wanna Talk About Me
  5. Whiskey Girl
  6. Who's That Man
  7. Wish I Didn't Know Now
  8. Beer for My Horses
  9. Somewhere Else
  10. I Won't Let You Down
  11. You Shouldn't Kiss Me Like This
  12. Don't Let the Old Man In

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