Kris Kristofferson was ‘a walking contradiction,’ a renegade and pilgrim surrounded by friends

Kristofferson, more comfortably than anyone, straddled the worlds of classic country music and Baby Boomer hippie culture. Janis Joplin was another close friend, and her howling rendition of Kristofferson’s “Me and Bobby McGee” would become a hit soon after her death in 1970. It was probably the best known version of any Kristofferson song, and he would use her arrangement of it when he played the song live.

Kristofferson also embraced kindred spirits of younger generations, like Sinead O’Connor.

A critic of the Roman Catholic Church well before allegations of sexual abuse were widely reported, O’Connor was loudly booed at a Madison Square Garden tribute to Bob Dylan in 1992, two weeks after ripping up a picture of Pope John Paul II while appearing on “Saturday Night Live.”

Kristofferson would come out and walk her off stage in solidarity and solace. Years later, he recorded “Sister Sinead,” in which he wrote, “And maybe she’s crazy and maybe she ain’t, But so was Picasso and so were the saints.”

His leftist politics may have been the greatest of his “contradictions,” coming from a country-singing Army veteran from Brownsville, Texas. He was a staunch supporter of Palestinians and made heated denunciations of many military actions in Central America and the Middle East from the stage, sometimes to the chagrin of audiences. He clashed at times with more hawkish stars like Toby Keith, though he counted many conservative country stars as friends and supporters.

Kristofferson said during a 1995 interview with the AP he remembered a woman complaining about one of his songs that talked about killing babies in the name of freedom.

“I said, ’Well, what made you mad — the fact that I was saying it or the fact that we’re doing it?’” Kristofferson said. “To me, they were getting mad at me ’cause I was telling them what was going on.”

To him, there was no contradiction, his political thinking was a reckoning for his military past.

“When you come to question some of the things being done in your name,” he told the AP in 2006, “it was particularly painful.”

No one was upset by the man’s blue-eyed gaze on screen, however. Legendary Western director Sam Peckinpah saw him as a perfect young outlaw to put alongside James Coburn in 1973’s “Pat Garrett and Billy the Kid.”

But he would be best known for playing the handsome love interest in films that centered on strong women: Ellen Burstyn in 1974’s “Alice Doesn’t Live Here Anymore,” directed by Martin Scorsese, and Barbra Streisand in the 1976 version of “A Star Is Born,” a role echoed by Bradley Cooper in the 2018 remake.

Streisand said on Instagram that she was developing “A Star is Born” when she saw Kristofferson on stage at the Troubadour in Los Angeles.

“I knew he was something special,” she wrote.

Scorsese said Monday that Kristofferson was “a damn good actor, a remarkable screen presence. Spending time with Kris when we made ‘Alice Doesn’t Live Here Anymore’ was one of the highlights of my life.”

The director said in a statement that he was listening to “Me and Bobby McGee,” “Just like half of the world.”

Kristofferson became a member of the Country Music Hall of Fame in 2004, but he had already been canonized beyond his own satisfaction when he became a member of the supergroup the Highwaymen in the mid-1980s, alongside Cash, Waylon Jennings, and Nelson, the only member now alive. To Kristofferson, it meant the men he had admired most regarded him as an equal.

“To be not only recorded by them but to be friends with them and to work side by side was just a little unreal,” Kristofferson told the AP in 2005. “It was like seeing your face on Mount Rushmore.”

Nelson and Cash’s daughter Rosanne were among the many artists who took part in a 2016 tribute concert to Kristofferson, joining him on stage for a group rendition of his song “Why Me.”

Kristofferson long thought about he would like to be remembered.

Another friend, Leonard Cohen, wrote in liner notes to his greatest hits collection that Kristofferson once told him he wanted the opening lines of Cohen’s “Bird on a Wire” on his tombstone: “Like a bird on a wire, Like a drunk in a midnight choir, I have tried, in my way, to be free.”

It’s apt enough, but another Kristofferson line from the “The Pilgrim” might serve just as well:

“The goin’ up was worth the comin’ down.”