In the final chapter of his life, Kris Kristofferson — the Rhodes Scholar turned songwriter, actor, and outlaw poet — reportedly turned inward.
According to insiders, the legendary artist kept a detailed personal diary chronicling not just his music and reflections, but his romantic history — including relationships that once made headlines and others that quietly unfolded behind the scenes.
And if those pages ever see the light of day, they may reveal far more than fans expect.
A Life of Passion — Written Down
Sources claim Kristofferson “wrote everything down” — his thoughts, emotional struggles, regrets, and especially the women who shaped his life.
Among those mentioned:
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Janis Joplin, with whom he shared a brief but electric connection before her tragic death in 1970.
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Rita Coolidge, his second wife, whose marriage to Kristofferson in the 1970s was both creative and turbulent.
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Barbra Streisand, his co-star in the 1976 film A Star Is Born, with whom he reportedly had a romantic chapter before his deeper relationship with Coolidge.
Insiders suggest the diary contains “love confessions” and emotional detail that could surprise many — perhaps even embarrass a few.
Marriages, Mistakes, and Redemption
Kristofferson married three times.
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His first marriage to Fran Beer ended in 1969.
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His high-profile marriage to Rita Coolidge lasted from 1973 to 1980.
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In 1983, he married Lisa Meyers — the woman who would remain by his side for more than four decades until his passing.
Those who knew him describe him as intense, passionate, and complicated — a man capable of deep love but also prone to self-destruction in his earlier years. He was open about battling alcohol before ultimately getting sober.
According to sources, the diary doesn’t only recount romances — it also reflects regret. Kristofferson reportedly wrote candidly about his darker years, his internal conflicts, and the toll fame and excess took on relationships.
A Complicated Soul Near the End
Kristofferson passed away on September 28 at age 88. In his later years, he lived quietly in Maui, Hawaii, spending time with Lisa, their children, and grandchildren. He retired from performing in 2021 after remaining active into his 80s.
If he sensed his time was nearing its close, some believe the diary may have been a way to clear his conscience — to set down the emotional truths of a life lived intensely.
For now, his family reportedly has no plans to publish the diary. But should that change, it could offer an unprecedented look at the private heart behind the public legend.
The Rule He Lived By
Kris once summed up his philosophy simply:
“Tell the truth. Sing with passion. Work with laughter. Love with heart. ’Cause that’s all that matters in the end.”
If his diary truly exists as described, it may be the most unfiltered version of that truth — written not for the stage, but for himself.