Inside Kris Kristofferson’s unlikely friendship with Taylor Swift

Kris Kristofferson, who died on Saturday, had an unlikely friendship with Taylor Swift for years.

The singer-songwriter, who was known for his role in “A Star Is Born” in 1976, died “peacefully” at his house in Maui, Hawaii. He was 88.

“We’re all so blessed for our time with him. Thank you for loving him all these many years, and when you see a rainbow, know he’s smiling down at us all,” his family said in a statement.

Kris Kristofferson and Taylor Swift, pictured here in 2012, had a friendship spanning over a decade before his death on Saturday. WireImage The “A Star Is Born” actor and the “Blank Space” singer started their friendship in 2009 when he presented her with an award at the Country Music Awards. WireImage

Kristofferson was beloved by many celebrities and legends in the music industry –– including Swift.

The “Me and Bobby McGee” writer and the “Cruel Summer” singer’s friendship dated back to 2009 when Kristofferson presented Swift with one of the several awards she won at the 43rd Annual Country Music Awards.

The following year, they grew a deeper bond while attending and performing at a benefit concert for Nashville’s Country Music Hall of Fame in Los Angeles, Calif.

Kristofferson presented Swift with an award at the time. Getty Images Kristofferson and Swift reunited in 2010 at a benefit for the Nashville Country Music Hall of Fame, as seen here with Lionel Richie. Alex Berliner/BEI/Shutterstock

Swift, who was 20 at the time, publicly declared her admiration for Kristofferson by telling the audience –– which included Kristofferson, Lionel Richie and Vince Gill –– “These are the best role models I could have,” according to a 2010 Los Angeles Times story.

The “Tortured Poets Department” songstress later got to have a more in-depth conversation with Kristofferson backstage, where they talked about their songwriting.

“I just know you are going to have the most wonderful career, and most wonderful life,” Kristofferson told her, according to a 2010 New York Magazine story.

Kristofferson told Swift backstage at the benefit, as seen here, that she would have a “wonderful career.” Corbis via Getty Images They later took the opportunity to pose for a sweet photo together, and he used it as his first Instagram post in 2022. LA Times / Instagram

Swift appeared starstruck and replied, “I could not ask for a better role model,” to which he quipped back, “Now, who’s the silver-tongued devil?”

Before Kristofferson left their chat, the author of the New York Magazine story asked Kristofferson if Swift could make it into the Nashville Country Music Hall of Fame, and Kristofferson laughed while teasing to the author, “She’s already in the Hall of Fame!”

Their conversation seemed to have a profound conversation on Swift, since she returned to her dressing room backstage with her mom, Andrea Swift, and raved about the entire ordeal.

The “Cruel Summer” singer, pictured here in August 2024, returned the favor by gushing about him being a good “role model.” Gareth Cattermole/Getty Images for TAS Rights Management Swift has yet to comment on Kristofferson’s death. Getty Images for TAS Rights Management

“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 to her mom.

During that same benefit, a photographer for the Los Angeles Times was taking some solo shots of Swift when she saw Kristofferson passing them and asked if he could join them for a few pictures.

The two posed for a sweet photo of them each holding half a heart with their hand to make a full hearthand.

The picture seemed to mean a lot to Kristofferson, as well, since he used it to make it his first Instagram post in February 2022.

Kristofferson, pictured here in 2006, died on Saturday. Peter Brooker/Shutterstock Kristofferson, pictured here in 1982, was 88. Richard Young/Shutterstock

“No better way to kick off Kris’ official @instagram account than with this picture of him and @taylorswift at the @officialcmhof “All For The Hall” concert benefit in 2010! #HappyValentinesDay,” his manager captioned the snap.

Swift, now 34, has yet to comment on Kristofferson’s passing since the family shared the information on Sunday.

However, other stars, like, LeAnn Rimes, Reba McEntire, Barbra Streisand and Dolly Parton all shared sweet tributes to their late friend.