Taylor Swift And Toby Keith’s Actual Relationship Was Downright Mysterious

Highlights

• Taylor Swift’s early success in both country and pop music made her a unique star who shattered records.
• Toby Keith played a significant role in Taylor Swift’s career by helping her sign with Big Machine Records.
• The true nature of their relationship is unclear, but their careers took off with their respective second albums.

If there is one star who could move seamlessly between the country and pop music worlds, of course it would be Taylor Swift. After impressing the world with her early hits like “Love Story” and “Tim McGraw,” she embarked on a pop career and has shattered every record she could ever have dreamed of.

Since Taylor Swift became such a big part of the country scene, it makes sense that she met Toby Keith, the overwhelmingly popular star whose serious health problems changed his career and led to his death in February 2024 from stomach cancer. But what kind of relationship did the singers actually have?

What Was Toby Keith And Taylor Swift’s Relationship?

While today the singer is a massive star known for writing songs about famous ex-boyfriends, back in the 2010s, Taylor Swift was a pre-teen who dreamed of making music for a living. That’s where Toby Keith came in.

Taylor Swift knew Toby Keith because he did business with Scott Borchetta, who started Big Machine Records. According to CMT Insider, Keith founded the music label Show Dog Records and he and Borchetta were co-workers. In a 2005 interview with CMT Insider, Borchetta explained, “I would encourage people to think of this as one label with two A&R sources. Toby’s the lead act.”

According to People, Toby Keith was a big reason why Taylor Swift signed with Big Machine Records. She sang for Keith and others at the label, and they could tell that she was talented. Although Keith and Borchetta stopped working together in 2006, he was there at the exact right time to realize that Swift needed to be a star.

As Swift explained to Nashville’s WSMV4:

“You’re in the room with him and you can feel it, 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 are just like, ‘Oh my God that’s Toby Keith.’”

While Keith was there when Swift was essentially discovered, it’s unclear how well they got along or if they maintained a relationship of any kind after she signed with Big Machine Records. Neither musician seems to have explained their connection beyond this one meeting.

Which Taylor Swift Albums Were Published By Big Machine Records?

• “Taylor Swift” (2006)
• “Fearless” (2008)
• “Speak Now” (2010)
• “Red” (2012)
• “1989” (2014)
• “Reputation” (2017)

As reported by Sportskeeda, many people are surprised that Swift hasn’t said anything about Keith’s passing, at least at the time of this writing. While countless celebrities have shared their thoughts on his death, she hasn’t made any public or official statements. Since Keith seems to have meant a lot to Swift and was there at the start of her amazing journey, people are confused.

It’s unclear if Swift and Keith kept in touch once he stopped his involvement with Big Machine Records. Fans can assume that he followed her career and was impressed by everything that she achieved.

At the very least, it seems likely that the singers ran into each other at events like the Country Music Awards. Swift might have seen Keith around more often when she was still making country/pop music rather than just pop.

Inside Taylor Swift’s First Record Deal With Big Machine Records

Since Toby Keith was an incredible part of Taylor Swift’s first record deal, it’s interesting to look back on how this came together. According to Entertainment Weekly, the story of Swift’s music career began when she was 11 years old. She went to Music Row in Nashville and asked for record deals, but as fans might expect, that didn’t go anywhere.

As Entertainment Weekly explained, the singer spent time writing songs and then got back out there. At the age of13, she got a record deal with RCA Records, although she left because she wanted to sing songs that she had written.

That’s not only an interesting part of her story, but also something that she has in common with Toby Keith. As explained by Al.com, when Keith got his first record deal in 1991 in Nashville, he wasn’t a fan of the songs and didn’t want it to come out. He said, “It didn’t sound like me; it didn’t have my feel to it and I wasn’t happy with the whole thing.”

According to Entertainment Weekly, when Swift impressed Scott Borchetta, he told her that he wasn’t at Universal anymore, but he could work with her at Big Machine Records.

While Taylor Swift is of course much older than she was when she got her first deal with Big Machine Records, she has never changed her approach to songwriting.

What Hit Songs Were On Taylor Swift’s First Album With Big Machine Records?

• “Teardrops On My Guitar”
• “Tim McGraw”
• “Picture To Burn”

In a 2014 interview with NPR, Swift talked about writing music and said:

“I wrote my first album when I was 14 and 15, so now we’re going on 10 years of making albums right now. The formula has never changed, in that I try to make an album that best represents the last two years of my life. People have essentially gotten to read my diary for the last 10 years.”

Taylor Swift and Toby Keith’s true relationship might be unknown, but they had something else in common: they both saw their careers really take off with their second albums. After Keith released his self-titled debut album in 1993, his second album “Boomtown” came out in 1994. Swift’s second album “Fearless,” which came out in 2008, featured singles like “You Belong With Me” and “Love Story.”

As Keith told Al.com, “The second record is the most important record you’ll do. If you come out and really smoke on a first single and stir up a stink in town, they think there’s a new kid and they wonder if he’s going to be a one-hit wonder. You have to have airplay to be successful.

Source: NewsFinale