Jennifer Aniston Gets Emotional Talking About Working with Late Kris Kristofferson: 'He Was Extraordinary'

Jennifer Aniston directed Kris Kristofferson, who died on Sept. 28 at 88, in her first short film and later costarred with him in 'He's Just Not That Into You'

Jennifer Aniston is recalling her time working with the late Kris Kristofferson, days after the beloved country singer-songwriter and actor died at 88.

During Aniston's Wednesday, Oct. 2 appearance on Jimmy Kimmel Live!, the Morning Show star remembered that she recruited Kristofferson to costar with Robin Wright in 2006's Room 10, Aniston's first short film as a director.

"I actually was lucky enough to direct my first short film and surprisingly when we asked him he said yes, he and Robin Wright, and it was one of the most special experiences I've ever had," she told host Jimmy Kimmel. As Aniston recalled, Kristofferson portrayed a man who visits his dying wife in a hospital in the final days of her life in the film.

"He broke our hearts, he was extraordinary," Aniston said. She also noted that Kristofferson later portrayed her onscreen father in the 2009 rom-com He's Just Not That Into You.

Related: Kris Kristofferson's Life in Photos

"He came to my 40th birthday party, his wife and he flew in," she added. "He [was] a lovely man. It's a huge loss."

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Kristofferson rose to fame in the 1970s as a singer-songwriter. All the while he appeared in movies like Pat Garrett & Billy The Kid (1973) and Alice Doesn't Live Here Anymore (1974), before he earned a big break in the 1976 remake of A Star Is Born, which costarred Barbra Streisand. He also recorded three albums with Johnny Cash, Waylon Jennings and Willie Nelson as The Highhwaymen in the 1980s and '90s.

Related: Barbra Streisand Shares Memories of Late A Star Is Born Costar Kris Kristofferson: 'Charming as Ever'

During Aniston's Jimmy Kimmel Live appearance, she further remembered that when she recruited Kristofferson to act in her 2006 short film, both she and Kristofferson were equally starstruck with each other because he had grown into a Friends fan.

"When we reached out to make the call, his wife had mentioned that they had just been binge watching Friends," she said. "They were shooting some movie in some foreign land, and I was so excited to meet him and he'd been watching Friends and we had this moment. It was adorable."

A representative for Kristofferson said he was surrounded by family when he died "peacefully" at his home in Maui on Saturday, Sept. 28. "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 shared in a statement.

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