Turn It Up - Kris Kristofferson Edition

Some recommendations from the late, great artist

Oct 07, 2024

Kris Kristofferson died last week after a truly remarkable career. In this special edition of Turn It Up, we pick out a few favorites from the Kristofferson catalog. (And one from its outer reaches.) We’ve also listed a few of our favorite tribute pieces as reading recommendations at the end.

“Why Me” (from Jesus Was a Capricorn, 1972)

Kris Kristofferson stands as one of country music’s most incisive, memorable, and influential songwriters; he’s the brains behind such masterpieces as “For the Good Times,” “Help Me Make It Through the Night,” “Me and Bobby McGee,” and “Sunday Morning Coming Down.” Kristofferson is also one of country music’s most God-awful singers—a point that wouldn’t be worth mentioning if only the unprecedented crossover success of his songs hadn’t allowed him to secure a recording contract in the first place.

Then again, on “Why Me,” Kristofferson’s vocal liabilities are the very qualities that make the record sing. “Why me, Lord?” he prays. “What have I ever done to deserve even one of the pleasures I’ve known?” His voice is so cracked you figure every note must hurt. His range is cramped yet still uncontrollable, his interest in phrasing appears negligible, and his relationships with pitch and key are downright abusive. That’s why, when he croaks “Lord, help me Jesus…I know what I am,” we know just what he means without him having to finish. What he is is just a man, deeply flawed, humbled, amazed. (Originally published in Heartaches by the Number: Country Music’s 500 Greatest Singles by David Cantwell and Bill Friskics-Warren, 2003) – DC

Kris Kristofferson – “Kiss the World Goodbye” (from Border Lord, 1972)

Lithe and slippery, drenched in a fatalism that’s both sad and smirking, “Kiss the World Goodbye” ends Kristofferson’s 1972 Border Lord with a goodbye song that recalls fellow Texan Roger Miller, another iconoclastic genius who remade country songwriting a few years earlier. Miller, of course, also covered Kristofferson multiple times, including the first release of “Me and Bobby McGee.” Kristofferson here returns the favor (stylistically at least) with “Kiss The World Goodbye,” a spare celebration of disengagement from a wounded outlaw. With twinkling finger-picked guitar guiding his way, Kristofferson sings vaguely and regretfully of his mistakes, heading down to the river (a la “Trouble in Mind,” a song this one recalls both thematically and musically) and letting it all slip away. A sad story, but one sung with such a light touch that it almost feels relaxed, or at least released to fate in a way that Kristofferson would explore in acting roles from Pat Garrett and Billy the Kid forward. As great as some of those films are, I’m not sure he topped “Kiss the World Goodbye” as a meditation. – CH

“Little Girl Lost” (from Border Land, 1972)

Boy, does Kris ever hate this woman. The verses rock and twang along in an echo of Blonde on Blonde, a record he saw come together firsthand between emptying the waste baskets at Columbia, and his lines come dosed with a Dylanesque venom as well: “She's drawing dirty pictures on the black side of your mind” and “You ain't about to touch her any deeper than her skin” and, best/bitterest of all, “You better count your fingers when she turns loose of your hand.” But then he catches himself, the music slows and turns music box fragile: “If you take her, take her easy, treat her gentle. She used to love me.” Little boy lost. – DC

“Okie from Muskogee” (from Live at the Philharmonic, 1992)

At this 1972 NYC gig, Kristofferson knows enough to leaves be the sing-along chorus to Merle Haggard’s “Okie from Muskogee” but pokes fun at the song by tweaking Merle’s verses. “We don’t smoke our draft cards in Muskogee / All we ever drop’s our BVDs,” Kristofferson begins. “We don’t know no hippies, queers or commies / Cuz we like livin’ right and bein’ free.” He’s in and out of the song in not much more than a minute and a half, a quick joke to break up a heavy show but also to make a political point. As the applause and laughter fade away, though, he makes another point: “We always have to do that one with apologies to our good friend Merle Haggard, who is neither a redneck nor a racist. He just happens to be known for probably the only bad song he ever wrote. He’s written many great ones. Very soulful dude.” It’s a testament to the respect he had for Kristofferson as a kindred soulful dude that Haggard took the note. In the last years of his life, Merle would often perform his signature song as if Kris’s revision had been in there all along: “We don’t shoot that deadly marijuana / We get drunk like God wants us to do.” – DC

Kris Kristofferson – “Me and Bobby McGee” (live at Farm Aid 1985)

There are so many great versions of “Me and Bobby McGee,” by Kristofferson and others. I love this lean and mean version from the first Farm Aid, where Kristofferson barrels through the song like he’s just now realizing how fucking great it is. He bounds around the stage, dressed in cool-rockin’-daddy black, singing those well-known lyrics and scaling that brilliantly simple melody with the support of his crack 1980s band The Border Lords. His craft and charisma are on vibrant display, and – with those Farm Aid banners hanging alongside the stage – so too is his commitment to a world beyond himself. “Freedom’s just another word for nothin’ left to lose” is the line that’s burned into cultural permanence, and justifiably so. But, to me, his opening question – “How’s your spirit?” – is just as indicative of an artist whose commitment to freedom and justice extended from the U.S. to Nicaragua to South Africa to Palestine and anywhere else his own spirit took him. – CH

“Between Heaven and Here” (from A Moment of Forever, 1995)

For A Moment of Forever, producer Don Was backed Kristofferson with a bunch of studio pro celebs (Jim Keltner, Benmont Tench, longtime FOK Stephen Bruton, etc.) for a glossy, vaguely roots rock approach that fits well enough with mainstream sounds of the moment from, say, Tom Petty or Mary Chapin Carpenter or Melissa Etheridge. Kris, his voice a bit back in the mix and punctuating his entreaties with sincere whispers, sounds fantastic. And when he’s joined by bluesy belter Jonell Mosser, who over emotes terribly her responses to his calls, Kris sounds not only more reasonable and rooted by contrast; he sounds great. “We can do better than this…,” Kris shouts, embracing this chance to be an anthemic arena rocker. “Maybe we’ll tear down the walls between heaven and here.” Great line. He’s singing specifically to a lover about better days within their reach, but he’s channeling a gospel impulse that has a mansion for each of us. – DC

Ghetto Mafia – “Straight from the DEC” (from Straight from the Dec, 1996)

Kristofferson’s enduring slow jam “For the Good Times” made its way from Ray Price to Al Green, and it’s Green’s version that Georgia rappers Ghetto Mafia sample and remix here, turning the luscious ode to breakup sex into an anthem for their Decatur hometown. Early ambassadors from the Atlanta-area hip-hop scene that would soon conquer the world, Ghetto Mafia MCs Nino and Wicked produced this track themselves, and they lay down inside Kristofferson’s melody as they help inaugurate a new generation of the overlaps between country, pop, and R&B that made the original song (in all its versions) so enduring in the first place. Adding emergent southern hip-hop into the mix – “This ain’t Compton, this Decatur” – Ghetto Mafia finds a new corner of the catalog in which Kris Kristofferson can make himself welcome. (Thanks to Jerome Dotson for hipping me to this track.) – CH

Kris Kristofferson – “I Do Believe” (from Lonesome, On’ry and Mean: A Tribute to Waylon Jennings, 2003)

From a 2003 tribute album, Kristofferson pays respects to his friend, colleague, and fellow Highwayman Waylon Jennings. Rather than tackle one of Jennings’ more famous songs, Kristofferson performs “I Do Believe,” a song from the last Highwaymen studio album that Jennings called “the best song I’ve ever written” and about which I feel almost as superlative. A discussion of faith beyond religion, of mercy and love without fear and condemnation, “I Do Believe” is a stately and subtly gorgeous song that explores spirituality with humility and generosity. Kristofferson’s voice – gruff, sweet, strong, soft – is perfect for Jennings’ spare lyrics, and the graceful, gracious arrangement provides warm complement. Touching the divine, yes, but anchored in the beautifully human. – CH

Kris Kristofferson – “This Old Road” (from This Old Road, 2006)

The best road songs might be the ones that take place when the road’s running out. Kristofferson first released “This Old Road” in 1986, in a slick full-band version on Repossessed. That take effectively captures the song’s valedictory side, but it’s a revelation to hear it in its twenty-years-later version, from the New West release that was his first studio album in over a decade. Here, especially as the lead-off track, “This Old Road” unsurprisingly becomes a reckoning with Kristofferson’s own aging. His voice is right up against the listener’s ear, talking straight to us (or maybe himself) as he remembers back through the past that brought him to a present marked both by satisfaction and regret. With Stephen Bruton’s delicate mandolin and background vocals walking with him, Kristofferson tenderly takes stock of a life defined now by “running out of time” and a “holy night [that’s] falling” even as the road continues in front of him. The twinkle in his voice suggests he might still have a few tricks left, and that the best of all may be forgiving himself for whatever’s gone wrong before. – CH

“From Here to Forever” (from Closer to the Bone, 2009)

“Here’s one I wrote for my kids,” he says, before singing a lullaby. Nothing more than a frail but persistent acoustic guitar figure, a hint of parlor piano, a harmonica solo, and old man Kristofferson, each wrinkle in his voice a gift, each imperfection perfect. “And, darlin’, if we’re not together, there’s one thing I want you to know / I’ll love you from here to forever and be there wherever you go.” He’s found something he’d lost once somehow, somewhere along the way. Not going to lose it again. – DC

Turn It Up - Kris Kristofferson Edition

Some recommendations from the late, great artist

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