Kris Kristofferson and Taylor Swift developed a special friendship years before his untimely death.

The singer-songwriter – best known for his role in “A Star Is Born” in 1976 – died “peacefully” at his home in Maui, HI, over the weekend. 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 posing together

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 began back in 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 an even deeper bond while attending and performing at a benefit concert for Nashville’s Country Music Hall of Fame in Los Angeles.
Kris Kristofferson and Taylor Swift hugging

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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.
Taylor Swift, Kris Kristofferson and Lionel Richie together

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. Kristofferson laughed while replying 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, gushed about her pal 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 said 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 by.

She asked if he could join them for a few pictures and the two posed for a sweet snap at the time.

The picture seemed to mean a lot to Kristofferson, as well, since he used it as his first-ever Instagram post back 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.

Other stars, like LeAnn Rimes, Reba McEntire, Barbra Streisand and Dolly Parton, have shared sweet tributes to their late friend amid the heartbreaking news.