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The two musicians have remained friends over the years and even shared the stage on multiple occasions. Keep reading for a breakdown of their biggest friendship moments.
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Chesney met Swift when she was an unsigned teenager.
Taylor Swift and Kenny Chesney both got their start in country music.Kevin Winter/ACMA2010/Getty Images for ACMA
Chesney wanted Swift to open for his 2007 tour, but she was too young.
Kenny Chesney performs in 2008 and Swift attends the 2009 CMA Awards.Allen J. Schaben/Los Angeles Times via Getty Images; Taylor Hill/WireImage
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They continued to interact at country music events and spoke highly of each other in interviews.
Taylor Swift and Kenny Chesney were both honored as CMT Artists of the Year in 2011.Rick Diamond/Getty Images for CMT
Chesney made a cameo during Swift's 2011 Speak Now World Tour.
Kenny Chesney and Taylor Swift perform together in 2011.Frederick Breedon IV/WireImage
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Swift returned the favor during Chesney's 2015 Big Revival Tour.
Kenny Chesney and Taylor Swift perform together in 2015.Rick Diamond/Getty Images for Kenny Chesney
Their live duet of "Big Star" was featured on Chesney's 2017 live album.
"Live in No Shoes Nation" was released in 2017.Blue Chair/Columbia Nashville
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Chesney praised Swift when she was named Time's Person of the Year in 2023.
Taylor Swift is Time's 2023 Person of the Year.Inez and Vinoodh for Time