Kris Kristofferson: 20 Essential Songs

One of Kristofferson’s defining songs, the mostly spoken track off his debut album tells the story of a songwriter who encounters Beelzebub in a bar and listens as ol’ Satan tries to quash his dreams. “If you waste your time a-talkin’/to the people who don’t listen/to the things that you are sayin’/who do you think’s gonna hear?” the devil taunts him. But the troubadour has the last laugh: drinking the beer that Lucifer bought him and making off with his song. It was a metaphor for the music business that Kristofferson disciples like Eric Church took to heart: Church even titled his recent one-man-show after the song. In a recitation intro, Kristofferson dedicated the song to Johnny Cash and June Carter — “who helped show me how to beat the devil,” he says. —J.H.

Kristofferson didn’t usually write on assignment, but when he received a call from Monument Records founder Fred Foster — who suggested a song title based off a secretary he knew — Kristofferson wanted to impress him. “I avoided him for three or four months because there were only thoughts running through my head,” he said in 1973. “I was driving back to New Orleans one night, the windshield wipers were going, and it started falling together.” Inspired by the Fellini film La Strada (Italian for “the road”), Kristofferson crafted a country stomper about two drifters. It became Janis Joplin’s only Number One hit, which Kristofferson only heard after her death in 1970. “Afterwards, I walked all over L.A., just in tears,” he later recalled. “I couldn’t listen to the song without really breaking up.” —A.M.

A masterwork ballad of longing, “Help Me Make It Throught the Night” was recorded by everyone from Elvis Presley and Jerry Lee Lewis to Tina Turner and, most famously, Sammi Smith. The latter had a Number One hit with a smooth-voiced rendition of the song, but Kristofferson’s version, off his self-titled 1970 debut, is hard to beat. The ache in his croak just can’t be beat, and when he sings the chorus, you genuinely fear he may not see the morning’s light. —J.H.

Pursue monetary wealth at your own peril, Kristofferson preached in this superb ballad about a Citizen Kane-type antagonist who prioritized fortune above all else — even his own wife. Darby learns this the hard way when, one night after balancing his books, he hears a strange noise in his home built of the “finest wood and stone” and went to investigate. What he saw shook him to the core: his beloved Helen Darby in congress with another man. “It only took one night to bring it down,” Kristofferson wrote of Darby’s estate, “when Darby’s castle tumbled to the ground.” —J.H.

Kristofferson wrote this sensual ode to the end of a relationship after going through the experience himself. The ballad became a standard the moment Kristofferson wrote it, recorded by all sorts of cross-genre heavyweights, from Al Green to Frank Sinatra to Elvis Presley to Ray Price, who turned the song into an all-time country single (and Number One hit) in 1970. “I tried to give it away for three years,” Kristofferson later said. “Publishers wouldn’t touch it because they said it was too dirty.” —J.B.

As the legend does, Kristofferson was so eager to get his songs in the hands of his hero Johnny Cash that he once landed a helicopter in the backyard of Cash’s Tennessee estate. It’s unclear how much such a tactic worked on the Man in Black, but Cash ended up giving Kristofferson his big break when he recorded “Sunday Mornin’ Comin’ Down,” his perfectly-told tale in which one man’s weekend hangover becomes an existential meditation of human loneliness. Kristofferson claimed he wrote it after his wife and kid moved to California without him. “Sunday was the worst day of the week if you didn’t have a family,” he said. —J.B.

The title track to Kristofferson’s 1971 album found him in the familiar confines of a bar; in this song, it’s the Tally Ho Tavern. But he’s not meeting Mephistopheles here like in “To Beat the Devil.” Instead, Kristofferson is the devil, a smooth-talking one that lands him and the women he meets in all kinds of carnal trouble — especially after the alcohol starts flowing. “All he’s good for is gettin’ in trouble and shifting his share of the blame,” Kristofferson sang, “And some people swear he’s my double and some even say we’re the same.” A handsome one at that. —J.H.

The title for this song was reportedly inspired by one of Kristofferson’s nicknames, Critter. According to the Kristofferson biography The Wild American by Stephen Miller, the musician and his daughter Tracy were spotted outside the Tally Ho Tavern on Music Row one day, when he heard someone say, “Look, here comes Critter and the kid.” The song itself is a heartbreakingly intimate and detailed distillation of love, loss, and nostalgia. It was a hit in 1968 for Roy Drusky. Kristofferson’s version is forlorn and poetic yet matter-of-fact, showing his deep admiration for the literary folk songwriting of Leonard Cohen, with his own weathered Texas beauty. —J.D.

Originally written for Waylon Jennings, whose version released before Kristofferson even recorded his, Kristofferson’s 1971 song became his first-ever charting single and one of only two Top 40 pop hits of his career. The song — with its perfect meter and devastating use of simile (“dreamin’ was as easy as believin’ it was never gonna end”) — became a case study in Kristofferson’s unmatched craft as a songwriter and was soon covered by Willie Nelson, Roger Miller, Skeeter Davies, and Tompall and the Glaser Brothers. When a very frail Kristofferson sang the song as a duet with Rosanne Cash in 2023, the heartbreak ballad transformed into a tear-jerking tribute to the elderly man who wrote it. —J.B.

At the opening of this song Kristofferson lists a bunch of buddies who inspired it, including Dennis Hopper, Johnny Cash, Jerry Jeff Walker, and Ramblin’ Jack Elliott. It’s an outlaw ballad in which the outlaw is an artist who’s seen his ups and downs — “wasted on the sidewalk in his jacket and his jeans/ Wearin’ yesterday’s misfortunes like a smile.” The song serves as a distillation of the ragged authenticity Kristofferson and his peers in the outlaw county movement would come to define. As he later said, “Well, there were a lot of people that the pilgrim stood for or that I felt fit into that category, and most of them were people who were serious about songwriting, but an awful lot of us just looked like we were out of work.” —J.D.  

With his 1972 album Jesus Was a Capricorn, Krisfofferson’s music took on a somewhat more polished sound compared to the spare, rugged feel of his first couple albums. He kicked it off with this hilarious, upbeat song, which uses the image of a hippie Jesus to take a shot at ignorance and hypocrisy. “Long hair, beard and sandals/And a funky bunch of friends/Reckon may just nail Him up/If he come down again” he sings, before he hits the chorus, “‘Cause everybody’s gotta have somebody to look down on.” The subtitle of the song honors singer-songwriter John Prine (whom Kristofferson helped out early in his career), and its irony, humor, and clever homespun turns of phrase, as well as Kristofferson’s delivery, show the influence of Prine. He once said, “If God’s got a favorite songwriter, I think it’s John Prine.” —J.D.   

“Why Me” was written by Kristofferson after attending a church service during a particularly low point in his life. With his future wife Rita Coolidge and future country star Larry Gatlin among the backup vocalists, Krisofferson sings about the life he’s lived and the change he needs to make. “Lord help me Jesus, I’ve wasted it,” he sings. The honest confessional power of the lyrics and the song’s gospel-steeped track touched a nerve with country fans. In summer of 1973, “Why Me” became his only Number One country hit. —J.D.

There are no winners in the title track of Kristofferson’s sixth studio album: the young, the old, the cheater, the cuckold, all stumble about in the lyrics to the tears-in-your-beer country ballad. “The moral doesn’t matter,” he sings against a choir of women’s angelic voices. “Broken rules are all the same/To the broken or the breaker/Who’s to bless, and who’s to blame?” The album was something of a commercial letdown for Kristofferson, and it followed Spooky Lady’s Sideshow, which also didn’t chart as well as his previous four albums. You can hear Kristofferson lean into feeling a little down on his luck on the title track to make the tension resonate more authentically. —K.G.

Kristofferson was known for his lyricism, not his melody. But “Stranger,” off 1975’s Who’s to Bless and Who’s to Blame, is one of his most catchy singalongs, produced by David Anderle (a Beach Boys associate) at Sunset Sound in L.A. Start with the very first two lines: “Maybe she was smilin’ in the mirror/Maybe I was too, ’cause I was stoned.” From there, he’s imploring the titular “stranger” to lead him wherever she wants. “And while we lay there, makin’ believe you love me/Stranger, could I believe in you,” he pleads. It’s any port in a storm, told in Kristofferson’s own poetic way. —J.H.

Right from the very first lyric, Kris Kristofferson makes his intentions clear: “If you’re feeling salty, then I’m your tequila.” Whichever jilted woman was lucky enough to be on the receiving end of Kristofferson’s pickup lines got an earful from Kristofferson in 1976. The song’s narrative is pretty clear cut: He’s out at a bar, a married woman looks upset, maybe a margarita would help. “There ain’t nothing sweeter than naked emotions,” he sings. “So you show me yours, hon, and I’ll show you mine.” What made his pitch even sweeter was all the song’s cheeky emotion that comes through his voice and those of his backup singers, which including Rita Coolidge, Gary Busey, Clydie King, and Billy Swan on the Surreal Thing album.–K.G.

Inspired by a scene in John Steinbeck’s The Grapes of Wrath, this early Eighties Kristofferson waltz would later be called one of the greatest songs in modern history by none other than Johnny Cash, who recorded his own version for 1985’s Rainbow. In just two verses, Kristofferson encapsulates humankind’s capacity for both meanness and ultimately, kindness. After two truck drivers judge a waitress for doing a good deed, they ultimately repay her with their own kindness in the form of a too-large tip. “It’s a brother helping a brother,” Kristoferson said. “Steinbeck had so much compassion.”–J.B.

Kristofferson was every bit the activist as he was a songwriter and championed social causes throughout his career. Arguably his most powerful song of that kind was “They Killed Him,” off the 1986 album Repossessed. Evoking Dion’s “Abraham, Martin and John,” it chronicled the efforts of peaceful warriors like Jesus, Gandhi, and Martin Luther King Jr. and the fate they all had in common: tragic deaths. Johnny Cash, Kristofferson’s compadre in the Highwaymen recorded his own version, as did Bob Dylan, whose rendition appears on Knocked Out Loaded. But Kristofferson’s version is particularly powerful — listen to him bellow, “My God they killed him!” at the end of each verse.–J.H.

A no-holds-barred anthem of leftist resistance from Kristofferson’s 1990 political concept album Third World Warrior. “They’re killing babies in the name of Freedom/We’ve been down that sorry road before,” he sings right at the top of the song, evoking political assassinations and America’s support for corrupt oppressive military dictatorships in Latin America and elsewhere. He also turns the lens on himself and by implication all of us, wondering “what my daddy would’ve done” in the face of such violent tyranny.–J.D.  

Nobody wants to feel his or her age, but Kris Kristofferson at age 69 had a way of helping people feel better about getting older. “Look at that old photograph, is it really you smiling like a baby full of dreams?” he sings on the title track of his 2006 album. “Smiling ain’t so easy now.” But then he acknowledges the struggle: “I guess you count your blessings with the problems that you’re dealing with today,” he sings in one verse, and in the chorus, “Ain’t you come a long way down this old road.” It’s a mature and realistic outlook, and he turns it into poetry later when he describes a rough patch as “one more rainbow for the road.” In 2009, actor Ethan Hawke called Kristofferson’s This Old Road record “perhaps his finest album” and told Rolling Stone it inspired him to want to make a documentary about the singer-songwriter.–K.G.

The title track to Kristofferson’s 2013 album was a stark portrayal of aging and decline released when the singer was 76 years old. The song was a moving meditation of what it means to grapple with the true realization they won’t be around forever. “At this point in your life,” he said after its release, “you gotta reflect on the fact that it will end. It’s happened to everybody else. We’re so reluctant to address it.”--J.B.