What We Know About Taylor Swift & Kris Kristofferson's Sweet Friendship

It's no secret Taylor Swift has her very own squad of famous friends, who follow the world-conquering pop star all over the world, but what you might not know is that dearly departed country legend and "A Star Is Born" actor Kris Kristofferson was an unofficial member of said squad. The legendary singer, who was previously misdiagnosed with Alzheimer's disease, died on September 28, 2024. Kristofferson had Lyme disease and fibromyalgia, but his cause of death has not been made public by his family as of this writing. Their statement simply confirmed that the country icon "passed away peacefully [...] at home," per People. Kristofferson was 88 years old, and when he first met Swift, he could've been her grandfather, yet the two forged a special bond regardless.

It all started at the 43rd Annual Country Music Awards, where Swift walked away with four trophies, including the coveted Entertainer of the Year award. Kristofferson happened to be one of the legends who presented a gong to Swift that night. The two became acquainted with a brief hug, with the "Shake It Off" hitmaker looking suitably starstruck. The duo's unlikely friendship grew into something special when Swift was invited to perform at the "All for the Hall" concert alongside Kristofferson and several other country legends. 

While the "I Knew You Were Trouble" songstress appeared to be well aware that she was a newcomer and probably felt a little out of place as a result, Swift plucked up the courage to join Kristofferson in performing his song "Me and Bobby McGee." Swift started quietly singing and playing along on her guitar as the song progressed. It was the beginning of what would turn into a lifelong friendship, and it's fair to say Kristofferson gave the pop star a major confidence boost early in her career.

When Taylor Swift joined Kris Kristofferson at the "All for the Hall" concert in 2010, he said something to her that is probably among the biggest reasons she's so successful today. "I just know you are going to have the most wonderful career, and most wonderful life," he reportedly assured her (via New York Magazine). It was at that moment that the newcomer blurted out her own admiration for Kristofferson's work and confessed that he was her ultimate role model, to which the "A Star is Born" star quipped in response, "Now who's the silver-tongued devil?" Swift, unable to believe that a country music legend basically anointed her for future success, rushed to tell her mom about the encounter. 

"I felt like I was going to pass out! He said so many nice things about my songwriting [...] I can't even remember everything he said; I blacked out a little bit," she gushed. Meanwhile, New York Magazine asked Kristofferson what he thought Swift's odds were of ending up in the Country Music Hall of Fame, and he seemed to think the answer was obvious, reasoning simply, "She's already in the Hall of Fame!" We wish we could've seen Swift's reaction when she read that quote after the fact.

It seems Kristofferson remembered that night just as fondly, because when he finally got an Instagram account in 2022, his very first post featured a picture of him and Swift at the "All for the Hall" concert. The "Bad Blood" hitmaker hasn't publicly commented on his death at the time of writing. Barbra Streisand, who co-starred in "A Star is Born" with him, described Kristofferson as "the perfect choice" for the role in a sweet Instagram tribute.