Renaissance man Kris Kristofferson - singer, actor, activist, veteran, Rhodes Scholar and "one of the greatest songwriters of all time” - has died at 88. Known for meticulously crafted songs of regret and longing - despite a voice "like a barking bullfrog" - he was also "an epic human with the biggest heart" who advocated for farmworkers, peacemakers, political prisoners, the Nicaraguan and other liberation struggles. What he wanted to emerge from his songs and shows, he said, was "a belief in the human spirit."

Kristofferson was born in Brownsville, Texas to a military family that moved around a lot, finally settling in San Mateo, California where he was a high-achieving student and short-story writer dubbed "Straight Arrow." In 1958, he won a Rhodes scholarship to Oxford University, where he got a master’s degree in English Literature and planned to write novels; in later years, he used to joke that between him and Bill Clinton, "We've cleared up any lingering myths about the brilliance of Rhodes scholars." Returning to the U.S., he enlisted in the Army; during a three-year-tour in West Germany, he boxed, learned to be a helicopter pilot and played in an Army band. On his return, he planned to accept a gig teaching at West Point until he took a fateful side trip to Nashville, where he quickly grew enamored of its burgeoning singer/songwriter scene and decided to join it. His mother disowned him, telling him that regardless of what he might achieve, it would never match "the tremendous disappointment you've always been."

But the good and dutiful student flourished in his new-found freedom, figuring if he didn't make it as a songwriter he'd get enough material to become a(nother) Great American Novelist. By then married with two kids, he sometimes wrote multiple songs a week, on the side working as a janitor at Columbia Recording Studios and as a part-time helicopter pilot; according to an apocryphal story, he once landed on Johnny Cash's lawn so he could hand him demo tapes of every song he'd written. His raspy "lawnmower voice" didn't help his performing career, but his songs - rich, mournful, introspective - quickly took off; starting in the 1960s, they were covered by covered by dozens of artists and earned multiple Grammys. Several became legendary: Help Me Make It Through the Night, Sunday Mornin’ Comin’ Down, and Me and Bobby McGee, with the iconic lines, "Freedom’s just another word/ For nothin’ left to lose." Tragically, he never heard Janis Joplin's version until October 1970, the day after she died.

Years later, Kristofferson said his songs' lyricism simply sprang from his experiences. As his marriage fell apart, he wrote Sunday Mornin’ Comin’ Down: "Cause there's somethin' in a Sunday/That makes a body feel alone." "Many of the people I admire are figments of our own imagination," he said. "I was just writing about what I was going through. One critic compared his craggy voice to the “grit and softness of ancient stone, worn smooth by time and elements." But his writing represented "a seismic shift" in country music before it got bastardized into the pop country Steve Earl calls "hip hop for white people who are afraid of black people." Many credit Kristofferson - troubadour, storyteller, member of the freshman class of "outlaw" singer-songwriters - with elevating and humanizing country music into a new and better art form. You could break down the country capital of Nashville, Bob Dylan once said, into "pre-Kris and post-Kris...He changed everything.”

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En route, Kristofferson became an actor, starting with Dennis Hopper’s The Last Movie in 1971. It was a commercial and critical flop, but he went on to over 50 films in the next two decades, including Scorcese's Alice Doesn’t Live Here Anymore with Ellen Burstyn in 1974and an award-winning turn in A Star Is Born with Barbara Streisand in 1976. After that role - a musician destroyed largely by alcoholism - Kristofferson stopped drinking, a move widely applauded. Alcohol, he said, had helped him feel “handsome and bulletproof"; it also almost derailed him. He went on to play, terrifically, a sadistic sheriff in John Sayles’ 1996 Lone Star. "He could dig for the simple truth of a character,” said Sayles, a deeply political filmmaker. "Just as important, Kris Kristofferson knows how to wear the boots." In 2018, he took on his final movie role as the estranged father of songwriter Blaze Foley in Ethan Hawke’s graceful Blaze. One reviewer praised Kristofferson's "a wonderful, albeit brief performance."

Kristofferson also long and consistently spoke out against injustice, beginning with a 1972 concert to benefit Cesar Chavez and the United Farm Workers. He protested nuclear power, supported Jesse Jackson's Rainbow Coalition, did benefits for Farm Aid and Amnesty International, played and spoke up for the release of Nelson Mandela, wrote a tribute to Gandhi, Jesus, and MLK Jr., performed at Obama's White House. In the 1980s, he traveled to Nicaragua in support of the Sandinista National Liberation Front, wrote songs about other Latin American liberation struggles, decried US. support of Contra terrorism in Nicaragua and the first Gulf War; that work inspired 1990's concept Album Third World Warrior: "They’re killing babies in the name of freedom/We’ve been down that sorry road before," with what became a catchphrase, “Don’t Let the Bastards (Get You Down).” When Bush invaded Iraq, he switched up some of the lyrics: "They're bombin’ Baghdad back into the Stone Age/Around the clock non-stop."

Kristofferson happily conceded other people sang his songs better than he could, though after joining longtime friend Willie Nelson for the 1984 film Songwriter, he argued he could still "sing better than Willie Nelson says I can." The next year, he and Nelson began to record and tour with fellow outlaws Waylon Jennings and Johnny Cash in the supergroup The Highwaymen; he once said that, when they invited him, he felt "like a little kid who'd climbed up on Mt. Rushmore and stuck his face up there." In 1991, on the brink of the Iraq War, they did an interview with New Zealand TV host Paul Holmes, who asked each what they thought was wrong with the U.S. They spoke of too much hate, bitterness, money for the military, "our obligation (to) straighten those things out." Not much, said Kristofferson, except it "reminds me a lot of the flag-waving and choreographed patriotism we had in Nazi Germany, with a lap-dog media cranking out propaganda that would make a Nazi blush. Other than that, we're doing pretty good."

Later he toured again with his band Border Lords, often playing small roadhouses. "Kris doesn’t know what the word 'commercial' means," said a friend. "He could go on stage performing Me and Bobby McGee every night. Instead (the) audience might hear 25 songs about the Sandinistas." Over time, he had triple heart bypass surgery and memory issues diagnosed as Alzheimer‘s that turned out to be Lyme disease. He released three quiet albums - This Old Road, Closer to the Bone, Feeling Mortal - and retired from it all in 2021. He died at home in Maui, Hawaii amidst his eight kids and his third wife Lisa Meyers, who helped navigate the last few years but balked at the term "manager": "He’s unmanageable. Even if someone tells him to have a good day, he’ll say, ‘Don’t tell me what to do.'" Still, he was there to console Sinead O'Connor being booed at a 1992 Dylan tribute concert after she'd ripped up the Pope's photo to protest sexual abuse in the Church. He was there to give her a hug and tell her, "Don't let the bastards get you down." "It costs nothing to be a decent human being," notes one fan. "God speed Kris Kristofferson."

The Pilgrim

And he keeps right on a changin' for the better or the worse
And searchin' for a shrine he's never found
Never knowin' if believin' is a blessin' or a curse
Or if the going up is worth the coming down
He's a poet he's a picker he's a prophet he's a pusher
He's a pilgrim and a preacher and a problem when he's stoned
He's a walking contradiction partly truth and partly fiction
Taking every wrong direction on his lonely way back home