Inside Kris Kristofferson's unlikely friendship with Taylor Swift

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

The singer-songwriter – best known for his role in 1976's “A Star Is Born” – died “peacefully” at his home in Maui, HI over the weekend. He was 88.

“We are all so blessed for our time with him. Thank you for loving him for all these many years and when you see a rainbow, know that he is smiling down on all of us,” his family said in a statement.

Kristofferson was loved by many celebrities and music industry legends – including Swift.

The friendship between the “Me and Bobby McGee” author and the “Cruel Summer” singer began in 2009, when Kristofferson presented Swift with one of the several awards she won at the 43rd Annual Country Music Awards.

The following year, their bond grew even stronger when they attended and performed at a benefit concert for Nashville's Country Music Hall of Fame in Los Angeles.

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

The “Tortured Poets Department” singer later had the opportunity to have a more in-depth conversation with Kristofferson backstage, where they discussed her songwriting.

“I just know you’re going to have the best career and the best life,” Kristofferson said, according to a 2010 New York Magazine story.

Swift seemed impressed and replied, “I couldn't ask for a better role model,” to which he quipped, “So 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 appeared to be an in-depth conversation about Swift, as she returned to her backstage dressing room with her mother, Andrea Swift, and gushed about the whole ordeal.

“I felt like I was going to faint! He said so many nice things about my songwriting… I can't even remember everything he said; “I lost consciousness a little bit,” she told her mother.

During the same fundraiser, a Los Angeles Times photographer was taking a few solo shots of Swift when she saw Kristofferson walk past them.

She asked if he could take some photos with them, and the two posed for a sweet snap at the time.

The image also seemed to mean a lot to Kristofferson, as he used it as his very first Instagram post back in February 2022.

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

Swift, now 34, has not yet commented on Kristofferson's death.

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