Kris Kristofferson Officially Retires After a Legendary, Six-Decade Long Career

The iconic outlaw and "Highwayman" quietly ended his epic career at the end of 2020

After a six-decade career in which he profoundly impacted the core definition of country, rock and roll, and the definition of effortlessly cool, Kris Kristofferson — the 85-year-old pillar definition of singer-songwriter excellence — has quietly retired.

On January 27, it was announced that Kristofferson ended his career at the end of 2020 and that Morris Higham Management is now administering his estate. Kristofferson’s son John now leads family business affairs, including KK Records, his indie record label. The icon’s colleague, Tamara Saviano, will handle public relations.

He was once quoted as saying, “Tell the truth. Sing with passion. Work with laughter. Love with heart. ’Cause, that’s all that matters in the end.” It can be argued that all of his other amazing quotes were published, heard, and seen in a way that redefined country and music industry excellence, in general.

As a songwriter, vocalist, and performer, Kristofferson’s name is inextricably linked to unexpected breakout career success rates for names including Johnny Cash, Waylon Jennings and Willie Nelson. Alongside his fellow Highwaymen, he preserved and elevated the legacy of outlaw country. Moreover, as an actor with Barbra Streisand in the 1976 film “A Star Is Born,” he helped cement her star power as a Hollywood leading lady. Plus, as the songwriter of “Me and Bobby McGee,” his words posthumously sealed Janis Joplin’s memory as a beloved wild-child hippie.

Kristofferson, a native of Brownsville, Texas, was a college athlete at Merton College who achieved becoming an Oxford University-educated Rhodes Scholar. Later, he was a military veteran who pursued songwriting as a career only after turning down an offer to teach English to cadets at West Point University. As if this was not enough, in the midst of a forever-relevant career in music, in 2013, Kristofferson acknowledged that he was suffering from memory loss. After misdiagnosing himself with post-concussion syndrome from his athletic career, he learned three years later that, in fact, his deterioration was caused by Lyme disease, which he picked up on a movie set in 2006.

The outlaw legend lives and now leaves a legacy that includes Grammy, Country Music Association, and Golden Globe Awards interspersed in a career that included 17 solo albums and nearly 100 films.

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