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Kris Kristofferson was one of the foremost icons in outlaw country music. His debut album, Kristofferson, is a classic, and tracks from it are still being made today. The songs written by Kris Kristofferson include “Me and Bobby McGee,” “For the Good Times,” “Sunday Mornin’,” “Comin' Down,” and "Help Me Make It Through the Night,” which other artists have covered over the years. Kris Kristofferson maintained relevance across generations; however, he retired in 2021 after his final concert at the Sunrise Theater in Fort Pierce, Florida. Sadly, Kris Kristofferson died in September this year after battling illnesses like fibromyalgia and Lupus in the years leading up to his passing. Kris Kristofferson’s life story Kris Kristofferson/ImageCollect Kris Kristofferson’s young life involved living in different towns due to his father’s military career, and after graduation from high school, he pursued his dreams of becoming a writer at Pomona College, where he received an honorary doctorate in fine arts in 1973. His experiences during these formative years are integral to understanding Kris Kristofferson's life story. The late music legend served in the US military until 1965, after which he moved to Nashville in hopes of promoting his music career. While attaining success in the entertainment industry, Kris Kristofferson announced his retirement in 2021, and at the time of his passing, Kris Kritofferson's net worth stood at $160 million. Barbra Streisand and Kris Kristofferson/Everett Before his enviable rise to fame, Kris Kristofferson had a dating stint with Barbra Streisand, who is a celebrity singer and actress herself. Barbra Streisand details her romantic relationship with her A Star Is Born co-star, Kris Kristofferson, in her memoir, My Name is Barbra. Theirs was a steamy romance that came with a lot of hickeys, which she tried to hide. They broke up before A Star Is Born, and they reportedly fought a lot during filming. Barbra paid tribute to the late star after his passing, saying he had always been special to her since she first saw him performing at the Troubadour Club in Los Angeles. Johnny Cash was another good friend and collaborator of Kris Kristofferson’s, and their work relationship blossomed on an unforgettable note. Johnny Cash got Kris Kristofferson, who was initially a janitor at his record label, to sit in for recording sessions. This almost cost Kris Kristofferson his humble job as the studio was out of bounds during work hours, but Johnny Cash stood up for him. Johnny Cash eventually helped him record 1970’s “Sunday Morning Coming Down,” which topped the Billboard US Country chart and changed Kris Kristofferson’s life. Kris Kristofferson/Everett How did Kris Kristofferson die? Kris Kristofferson died at 88 while surrounded by family at his home in Maui. Kris Kristofferson’s family noted that he passed away peacefully and wanted the first three lines from Leonard Cohen's “Bird on the Wire,” which reads, “Like a bird on the wire / Like a drunk in a midnight choir / I have tried in my way to be free,” to be written on his gravestone. Kris Kristofferson’s wife, Lisa Meyers, whom he married in 1983 after two previous divorces, shares five children with him in addition to his previous three from his ex-wives. Altogether, Kris Kristofferson was a proud father of eight, and most of his kids have followed his path in show business with acting, music, and wrestling careers, while a few of them prefer life outside the spotlight. During his final years, he experienced cognitive challenges and memory loss, which doctors claimed was the onset of dementia or Alzheimer’s, which was later discarded as a misdiagnosis. Lisa said he was on Alzheimer’s medication for a bit, but his memory improved when he stopped the treatment. He was diagnosed with Lyme disease in 2016, which his fibromyalgia may have indicated in 2004. These health struggles were part of what shaped Kris Kristofferson's life story as an artist who persevered through adversity. Kris Kristofferson reflected on retirement during these times but never officially quit working until 2020. He left his business affairs to his son John and his estate to Morris Higham Management. Kris Kristofferson/ImageCollect Kris Kristofferson had come to terms with the state of his health, which he had juggled with work for decades. Memory loss meant he could no longer remember some of his lyrics, but his manager, Tamara Saviano, said his music would go on in the form of archival or tribute work. Despite the long list of health issues Kris Kristofferson faced, his family did not specify his cause of death. They noted that he died peacefully in his Hawaii home and was surrounded by loved ones as he took his last breath at 88 on September 28.