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How Toby Keith Played An Important Role In Signing Taylor Swift To Her First Record Deal
It’s no secret that Toby Keith was one of the most iconic and influential figures in American country music. The Oklahoma native rose from humble beginnings to become a powerhouse in the industry, known for his commanding voice, songwriting talent, and fiercely patriotic spirit.
Toby Keith burst onto the country music scene in 1993 with his debut single, “Should’ve Been a Cowboy.” The song quickly became a massive hit, eventually earning the title of the most-played country song of the 1990s. It was a fitting introduction to a career that would span more than 30 years, filled with chart-topping success and deep cultural resonance. Over the course of his career, Keith released more than 20 studio albums and saw over 60 singles chart on the Billboard Hot Country Songs list. More than 20 of those songs went to No. 1, including fan favorites like “How Do You Like Me Now?!,” “I Love This Bar,” “Courtesy of the Red, White and Blue (The Angry American),” and the duet with Willie Nelson, “Beer for My Horses.”
Beyond his commercial success, Keith received numerous accolades for his work. He won multiple Academy of Country Music awards, including Entertainer of the Year, and earned recognition from the Country Music Association and Billboard. In 2015, his songwriting achievements were honored with induction into the Songwriters Hall of Fame.
But more than music, a defining aspect of Keith’s public persona was his deep patriotism. Following the events of September 11, 2001, he became known for songs that expressed pride in American values and support for the military. He traveled extensively with the USO, performing for more than 250,000 troops overseas, and was awarded the Spirit of the USO Award for his commitment to the armed forces. Keith also used his platform for philanthropy. He founded the Toby Keith Foundation, which provides support to children battling cancer. One of the foundation’s key initiatives is OK Kids Korral, a home in Oklahoma City where pediatric cancer patients and their families can stay free of charge during treatment.
But what might be a secret to some is that the Big Dog Daddy was actually instrumental in the discovery of former country singer, and current pop megastar, Taylor Swift. Yep, the biggest star in all of music got her big break thanks to the late, great Toby Keith.
Signing Taylor Swift
Back in 2004, Taylor Swift was just a teenager with a guitar, writing songs in her bedroom and singing around Nashville at places like the iconic Bluebird Cafe, when she was first discovered by a DreamWorks Records executive named Scott Borchetta. DreamWorks was sold to Universal Nashville that year, but Borchetta was looking to leave and start his own record label. He was immediately impressed with Swift’s talent, especially at such a young age, and wanted to sign her to his new record label… but he hadn’t launched it yet.
Enter Toby Keith.
In 2005, Toby had left his former label, DreamWorks Records, and founded his own record label, Show Dog Nashville. The move resulted in the closing of DreamWorks, but it provided Toby with the infrastructure to not only release his own music but also sign artists like Randy Houser, Trace Adkins and Joe Nichols… and it was that partnership that helped Borchetta get his own record label off the ground.
DreamWorks shuttered and was merged into Universal Music Nashville, and Borchetta left to start his own label, Big Machine Label Group. The label was founded as a joint venture between Big Machine and Show Dog Nashville, with the two labels to be “sister companies,” and Big Machine essentially used all of Show Dog’s staff while it was first getting started.
And the first artist signed to Big Machine? Taylor Swift. Talk about hitting a grand slam in your first at bat. Borchetta brought Taylor into the office to perform for Toby and he was immediately impressed with her talent as well. He agreed with Scott, and they offered her a contract.
Back in 2005, Taylor even talked about signing to Toby Keith’s label, saying she was starstruck but the country music icon:
“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.'”
The partnership between Big Machine and Show Dog didn’t last, with the labels splitting in 2006 and Toby retaining equity in Big Machine for the investment he had made. But if it wasn’t for Toby Keith and Show Dog, Big Machine wouldn’t have been able to get off the ground when it did, and wouldn’t have been able to sign Taylor Swift to her first record deal.
Big Machine would go on to sign acts like Florida Georgia Line, Carly Pearce, Riley Green, as well as deals with established acts like Hank Jr., Reba, Tim McGraw and more.
And Taylor, well… we all know what she went on to accomplish.The post How Toby Keith Played An Important Role In Signing Taylor Swift To Her First Record Deal first appeared on Whiskey Riff.
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