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Taylor Swift’s Most Memorable Early Collaborations: From Country to Hip Hop to Pop

When Taylor Swift first strummed her guitar and sang about Tim McGraw, few could’ve predicted she’d one day share the stage with him, plus other music superstars. From a teenage…

Singers Taylor Swift and Tim McGraw perform during the 2013 CMA Music Festival
Photo by Christopher Polk/Getty Images

When Taylor Swift first strummed her guitar and sang about Tim McGraw, few could’ve predicted she’d one day share the stage with him, plus other music superstars. From a teenage songwriter writing about love and heartbreak to becoming a global icon, Swift’s journey is marked by memorable collaborations.

Taylor Swift’s Full Circle Moment: “Highway Don't Care” with Tim McGraw and Keith Urban  

Swift's collaboration with McGraw and Keith Urban in 2013 on “Highway Don’t Care” represented a full-circle moment for the young singer-songwriter, who had debuted with a single after the country singer and actor. In an interview, McGraw admitted he wanted to collaborate with Swift, saying, “I knew I wanted Taylor to sing that part because it just fit perfectly. I wanted to do a song with Taylor for a long time.”  

The track also featured another country music legend, Keith Urban, on guitar.  

Tim McGraw - Highway Don't Care ft. Taylor Swift, Keith Urban  

Chart Performance and Commercial Success  

“Highway Don’t Care” debuted early, thanks to unsolicited airplay, which means it entered the charts seven weeks before its official radio add date. It peaked at No. 1 on the U.S. Country Airplay. Compared to other country duets of the early 2010s, “Highway Don’t Care” stood out not only for the superstars behind it, but also for its record audience reach and relatable lyrics about driving distractedly with a million thoughts, and the radio playing a song that seemed to be about what you’re going through.   

The first verse goes, “Bet your window's rolled down and your hair's pulled back / And I bet you got no idea you're going way too fast / You're trying not to think about what went wrong / Trying not to stop 'til you get where you goin' / You're trying to stay awake so I bet you turn on the radio.”  

The track also earned multiple accolades, winning at the 2013 American Country Awards, the Country Music Association Awards, and the 2014 Academy of Country Music Awards, as well as receiving a Grammy nomination. These milestones reinforced McGraw’s dominance and helped establish Swift’s credibility with country music fans.  

Other Notable Collaborations fro Swift's Early Years

Swift’s collaborations might have peaked with McGraw and Urban, but she did not stop with them. She also collaborated with artists from other genres, including with B.o.B on “Both of Us,” a critically-acclaimed song that talks about racism and bullying: “'Cause if life is an uphill battle / We all tryna climb with the same ol' ladder / In the same boat, with the same ol' paddle.”  

B.o.B - Both of Us ft. Taylor Swift [Official Video]  

“Two Is Better Than One,” Swift’s collaboration with Boys Like Girls from 2009, was also commercially successful and reached No. 18 on the Billboard Hot 100 and Canadian Hot 100.  

Her previous personal relationship with John Mayer might have overshadowed their professional collaboration, but their 2009 duet “Half of My Heart” was significant with Mayer. The “Your Body is a Wonderland” singer described her as having “one of the best work ethics I've ever seen on somebody.”  

John Mayer - Half of My Heart (Official Video)  

Swift will collaborate with more artists throughout her career, but her early collaborations when she was still a country artist proved her versatility and creativity by partnering with established artists from different genres. Her impact on the evolution of the music industry and genre-blending paved the way for a new generation of singer-songwriters.