How Toby Keith helped launch Taylor Swift’s career

Country singer Toby Keith has died of cancer at 62 – and in the wake of his passing, anecdotes from his life are emerging, including his surprising role in Taylor Swift’s career. 

Although Swift, 34, is one of the biggest pop stars in the world, in 2005, she was an unknown high schooler with “Wildest Dreams” of making it big. 

Keith, the “Should’ve Been a Cowboy” singer, was an established star at the time.

The record label Big Machine Records was launched by former DreamWorks executive Scott Borchetta. Keith launched a record label, Show Dog Nashville, the same year Big Machine launched, and the two labels worked closely together. 

“I would encourage people to think of this as one label with two A&R sources,” Borchetta told CMT Insider at the time. “Toby’s the lead act, and we’ve got an incredible opportunity with all the resources that he brings and the music that he loves and his vision for what he wants to do.”

According to the Tennesean, it was Borchetta who signed Swift — but, Keith helped him launch the label that did it.

In a 2005 interview with WSMV 4, Nashville, featuring a 15-year-old Swift, the singer explains how Keith was instrumental in getting her signed when she was a virtual unknown. She also spoke about the importance of their partnership early in her career.

“You’re in the room with him and you can feel it,” Swift said of her mentor.

“There’s a power there and you’re just like ‘Oh my God!’ I don’t think I’ll ever get to a point where I don’t see him and go, ‘Oh my God, that’s Toby Keith!’ Most people find out what they are going to do when they are in college and that’s great, you know, but for me it just came a little earlier,” she added.

Keith also retained stakes in Big Machine Records even after the labels became more separate, so he reportedly earned money from Swift. 

In November 2018, Swift completed her contract with Big Machine Records after six albums. In 2019, Scooter Braun’s company, Ithaca Holdings, purchased Big Machine – leading to a public feud between Braun and Swift and causing Swift to release re-recordings of songs from her first six albums, which she dubbed “Taylor’s version.” 

Keith’s death was announced Tuesday in an Instagram post, reading that Keith “passed peacefully” Monday evening while “surrounded by his family.”

“He fought his fight with grace and courage,” the statement read. “Please respect the privacy of his family at this time.”

 Swift has not made a statement about Keith’s passing. 

“Taylor Swift has an opportunity to really drive this country insane by thanking Toby Keith for believing in her from the jump (and recording a tribute version of “I Wanna Talk About Me”)” one fan posted on X. 

“NGL, a Taylor Swift tribute to Toby Keith could bring a lot of healing to America,” another fan commented. 

“RIP to the great Toby Keith — all you Swifties out there remember, without Toby there may have never been no Taylor Swift,” another fan proclaimed.