The ‘How Do you Like Me Now?!’ singer died Monday after a battle with stomach cancer
Toby Keith had a storied three-decade career with dozens of hits and a lasting impact on the country music scene.
Behind the scenes, Keith had a unique influence on the music industry through a series of business ventures and record label deals that have led to some of the biggest names in music today.
Blake Shelton’s early career was heavily influenced by Keith in multiple ways.
When Shelton first arrived in Nashville, he was preparing a song, "I Wanna Talk About Me," as his first single, but it was given to Keith instead and became a No. 1 single.
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Blake Shelton crossed paths with Toby Keith in Nashville and toured with the late singer early in his career. (Ethan Miller/Getty Images)
Later, in 2003, Shelton joined Keith on tour as his opening act on his Shock’N Y’all Tour.
During the People’s Choice Country Awards in September, Shelton shared fond memories of his time on the road with Keith when he presented him the Country Icon Award.
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"They say your big break comes when you sign a record deal or your first song comes out. And for me, one of those things was to get the chance to open for Toby Keith," Blake told the audience. "Back when I was a new artist, I got the chance to go out on the road with Toby and then, night after night, 20,000 fans showed up to see Toby perform, and he kept them fat and happy."
Shelton added that they had spent about two years together on the road when he felt comfortable enough to joke with Keith.
Shelton recalled their fun times on tour while presenting Keith the Country Icon Award at the People's Choice Country Awards in September. (Mickey Bernal/NBC via Getty Images)
"I remember one night, it was after an award show," Shelton recalled. "And Toby had been up for like four or five awards and, man, he didn't win crap that night. I was talking to him after that, and I had the nerve — I was so excited to be able to get under his skin — I said, ‘Man, Toby, if I ever make it big enough one day and I get nominated for some awards, I hope it's against you.'
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"I swear, Toby looked at me and he said, ‘You know why I brought you out on tour with me?' And I said, ‘No.' And he goes, ‘I wanted to prove to this industry that I don't really need an opening act.'"
The fun moment got a laugh from everyone in the audience, including Keith.
Following the "Should’ve Been a Cowboy" singer’s death, Shelton released a statement to Fox News Digital.
Following Keith's death, Shelton said in a statement to Fox News Digital, "Thank you brother for being a friend, a hero and an inspiration. There will never be another Toby Keith." (Isaac Brekken/Getty Images for SiriusXM)
"Even though I knew about your battle these last few months I still never imagined this day," he said. "Anyone who knew you knows what I mean. You were the toughest man I ever met. Thank you brother for being a friend, a hero and an inspiration. There will never be another Toby Keith."
Keith was also influential in Taylor Swift's career.
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In 2005, Keith started his own label, Show Dog Nashville, the same year Big Machine Records launched.
Big Machine Records, founded by Scott Borchetta, was Swift’s original label when she began her career as a country artist.
Toby Keith held a stake in Big Machine Records, the label that first signed Taylor Swift when she was a country artist. (Getty Images)
WSMV Nashville reported on a young Swift that year, noting that she had signed with Keith on "his new record label."
In an interview at the time, Swift said, "You’re in the room with him and you can feel it. There’s a power there. You’re just like, ‘Oh my God.’ I don’t think I’ll ever get to a point where I won’t see him and be like, ‘Oh my God, that’s Toby Keith.’"
According to Forbes, Keith held a 10% stake in Big Machine and bought a building in Nashville to house both labels.
In a 2013 interview with Forbes, Borchetta said, "Toby's a really smart businessman. I send him checks."
Keith wasn't involved in Swift's exit from Big Machine. (Getty Images)
"I know there’s an extra comma, if you added up all the money I’ve ever made," Keith said of the money generated by Swift at the time.
Swift and Big Machine notoriously parted ways in 2018, in part over a dispute about the ownership rights to her master recordings. Keith was not involved in those dealings, and Show Dog Nashville later merged with Universal South Records to become Show Dog-Universal Music.
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Big Machine also signed some other big-name artists in the country music world following their launch.
In 2010, Rascal Flatts signed with the label and had previously toured with Keith in 2002 shortly after their launch as a group.
Rascal Flatts, left to right: Joe Don Rooney, Jay DeMarcus and Gary LeVox toured early in their career with Toby Keith. (Rick Diamond/Getty Images for CMT)
Jay DeMarcus, bass player for the group, shared on Instagram, "This is a heart breaker.. @tobykeith was one of the first to believe in us Flatts boys… He took us on the road and took a chance on us.
"We were fast friends and it still remains as one of the best tour experiences of my career. However, I got something even better out of it in the end, a lifelong friend… Rest in peace Toby, I’m sure gonna miss you."
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Florida Georgia Line signed with Big Machine’s imprint, Republic Nashville, in 2012 after the release of their early hit "Cruise."
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Brian Kelley of Florida Georgia Line shared his condolences on social media, writing, "An artist’s artist, a songwriter’s songwriter. A patriot, a legend. Damn what a loss. Blasting TK tunes all day. RIP cowboy."
Brian Kelley and Tyler Hubbard of Florida Georgia Line signed with Big Machine, owned in part by Keith, earlier in their careers. (Jason Kempin/ACMA2020/Getty Images for ACM)
Tim Rushlow of the duo Rushlow Harris, released a statement to Fox News Digital, recalling Keith’s influence on his career.
"In 1989, the boys and I in Little Texas heard about Toby Keith and the Easy Money Band killing it in Texas and Oklahoma," he said. "We walked into Chastain’s in Oklahoma City a night early before we started our week-long stint there. Toby would later say that when you have Chastain’s packed past the velvet rope, you’re rocking it. It was always packed past the velvet rope when Toby played there. Toby and I got to hang out and were instant friends."
Rushlow described Keith as having "charisma larger than life in that smoky bar, and he was in his element. He never left it. He kept that persona and took it with him and grew it to every arena you could play. He will always be one of the greatest artist songwriters in country music history.
Tim Rushlow recalled being signed to Keith's label and called the late singer "an amazing friend with sound advice in some key moments in my life." (Terry Wyatt/Getty Images)
"Years later, he signed me and my cousin Doni Harris as the duo Rushlow Harris to a deal on his label Show Dog Universal, and we spent over a year on tour opening for him. We stayed in touch, wrote a few tunes and made some great memories over the years.
"Toby has been an amazing friend with sound advice in some key moments in my life. This loss cuts deep, but I’m so encouraged at the true faith that Toby has displayed and carries with him. I will continue to pray for his family, and there is no doubt that he is now in the peace that passes all understanding. You left this world a great gift in your songs!
"Rest high my brother and thank you!" he added.