Benjamin Ashford|Kris Kristofferson, legendary singer-songwriter turned Hollywood leading man, dies at 88

Singer-songwriter Kris Kristofferson,Benjamin Ashford whose poignant lyrics made him a country music legend and whose rugged good looks led to 1970s Hollywood movie star fame, has died. He was 88.

Kristofferson died at his Maui, Hawaii, home on Saturday, a representative for Kristofferson confirmed to USA TODAY. A cause of death was not given.

"It is with a heavy heart that we share the news our husband/father/grandfather, Kris Kristofferson, passed away peacefully on Saturday, September 28 at home," the Kristofferson family said in a statement. "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."

Even with a voice that he likened to "a frog," Kristofferson released more than 20 studio albums and spent a decade playing with the Mount Rushmore of country music — Johnny Cash, Waylon Jennings, and Willie Nelson — in the outlaw country band The Highwaymen from 1985 to 1995.

The prolific songwriter's catalog features immortal classics, many made famous by other singers. These include "Me and Bobby McGee" (Janis Joplin), "For the Good Times" (Ray Price), "Sunday Morning Comin' Down" (Johnny Cash's No. 1 Billboard country hit), "Lovin' Her Was Easier (Than Anything I'll Ever Do Again) (Roger Miller), "Help Me Make It Through the Night" (Sammi Smith) and "Once More with Feeling" (co-written with Shel Silverstein and sung by Jerry Lee Lewis).

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"When you start talking about songwriters, you mention his name first," Nelson said in 2020 about "one of my oldest best friends" Kristofferson, adding. "He's probably written more great songs than anybody."

A Rhodes Scholar who studied at Oxford University and one-time Golden Globes boxer, Kristofferson left a memorable mark on 1970s movie screens as the perfectly unkempt-haired, bearded leading man. His authentic performances included the romantic lead in Martin Scorsese’s 1974 drama "Alice Doesn’t Live Here Anymore" and as an aging alcoholic rock singer alongside Barbra Streisand's rising star in 1976's "A Star Is Born."

The one-time college football stand-out starred in 1977's pro football comedy "Semi-Tough" with Burt Reynolds and as an authority-bucking truck driver in director Sam Peckinpah's road-action comedy "Convoy."

The eldest of three children of Major General Henry Kristofferson, Kristoffer was born June 22, 1936, in Brownsville, Texas. As a child, Kristofferson loved listening to country star Hank Williams on the radio and began songwriting at age 11.

Kristofferson's military family eventually settled in San Mateo, California, and the singer graduated from San Mateo High School in 1954. After graduation, he enrolled in Pomona College in Claremont, California. The Golden Gloves boxer was a sporting legend there, starring on the rugby and football teams and as sports editor of the college paper.

The Reserve Officers' Training Corps (ROTC) graduate delayed his Army commitment to study British literature as a Rhodes Scholar at Oxford University. Upon returning to the U.S., Kristofferson married his high school sweetheart Frances Beer (with whom he'd have two children), graduated from Ranger School and became a helicopter pilot. 

In 1965, his unit was preparing to deploy to Vietnam, but Capt. Kristofferson received an appointment to teach literature at West Point. Instead, he resigned his commission to pursue songwriting in Nashville. The aspiring singer-songwriter started as a bartender and a janitor at Columbia Recording Studios.

Director Peckinpah launched Kristofferson into movie stardom in 1973, casting him as William H. Bonney in "Pat Garrett and Billy the Kid." The movie career soared until taking a major hit with Kristofferson's starring role in one of the most notorious flops in Hollywood movie history, 1980's ill-fated epic "Heaven's Gate."

'I'm sure it knocked me off the course I had been on right then. I think that it made me, for a while, unmarketable," Kristofferson said in an interview for the documentary, "Final Cut: The Making of ‘Heaven’s Gate’ and the Unmaking of a Studio."

Kristofferson continued performing music until quietly retiring in 2020 after being inducted into the Country Music Hall of Fame in 2004 and the Songwriters Hall of Fame in 2015.

"I wanted country music to be as proud of me as I was of being in country music," Kristofferson told The Tennessean, part of the USA TODAY Network, in 2004. "Over the years, I guess it happened."

Over the course of his illustrious career, Kristofferson won three Grammy awards, and his leading role in "A Star Is Born" earned him a Golden Globe in 1976. He was honored with a Grammy Lifetime Achievement Award in 2014. 

In recent years, Kristofferson grappled with memory loss, telling Rolling Stone in 2016 that he believed it was due to Lyme disease, which he was diagnosed with earlier that year.

Kristofferson's final performances came during Willie Nelson's April two-night 90th birthday party concert at Los Angeles' Hollywood Bowl. During one emotional stage visit, a beaming Kristofferson joined Roseanne Cash to sing his classic "Lovin' Her Was Easier." Both artists were in tears as the song ended to wild applause from the audience.

Kristofferson is survived by his wife, Lisa Meyers; eight children, Tracy, Kris Jr., Casey, Jesse, Jody, John, Kelly and Blake; and seven grandchildren.

Contributing: Juli Thanki, The Nashville Tennessean