6 Kris Kristofferson songs that changed Nashville and left a lasting impact

Artists may top the charts, or fill stadiums, but few have such an impact that they inspire a new direction for an entire genre. Starting with a series of songs in the 1960s and then, finally, his self-titled debut album in 1970, Kris Kristofferson gave country music the wake-up and shake-out it so desperately needed.

Kristofferson, who died this past Saturday (Sept. 28, 2024) at age 88, was part of a new crop of country singer-songwriters (Willie Nelson, Roger Miller, Mickey Newbury among them) working hard to get noticed and at the same time bringing new, folk- and rock-inspired ideas to the Nashville establishment. This wasn’t just about covering the Beatles or a Bob Dylan song here and there (which plenty of artists had done), it was taking a whole new approach to the writing itself.

It was Kristofferson’s music in particular that broke the mold. Songs like “Help Me Make It Though the Night,” “Me and Bobby McGee,” and “Sunday Mornin’ Comin’ Down” brought new and different energy. Sometimes dark, other times lustful, occasionally funny, and always deeply honest, his lyrics were direct, his melodies immediately captivating, and the emotions you were left with were raw and visceral. Whatever the mood or the subject at hand, Kristofferson’s songs weren’t afraid to pull back the covers.

“You can look at Nashville pre-Kris and post-Kris,” Bob Dylan said during his 2015 MusicCares speech, “because he changed everything.”

Kristofferson loved country music, but he was an outsider. And he looked the part, too: his long hair, jeans, scruffy appearance didn’t fit the buttoned-up style of so many Nashville stars. (Keep in mind that he broke on the scene a few years ahead of the Outlaw Country movement.) But, his music cut through all those differences – Music Row was starved for songwriting that was this smart, down-to-earth, honest, and fearless. Before long, Kristofferson was winning awards and finding himself at the top of the charts. He also found Hollywood calling – and it turned out, he was pretty talented in that department as well.

Kristofferson’s legacy is massive (as Sturgill Simpson once told Nathaniel Rateliff, “that’s the coolest motherf***er that ever lived”), and it will take years to unpack the influence he’s had on music, film, and culture as a whole. So let’s start where he started. Below are 6 Kris Kristofferson songs that’ve left a lasting impact. 

1 – Sunday Mornin’ Comin’ Down 

Drinking songs had been a go-to staple of country music artists for decades, but with this song, things felt different, “I woke up Sunday morning with no way to hold my head that didn’t hurt,” Kristofferson sings in the opening line. “And the beer I had for breakfast wasn’t bad, so I had one more for dessert.” It’s down and out on one hand, a little funny on the other – but most of all, it’s self-aware, introspective. We are right in this person’s head. We understand the weight of the hangover they feel, but also, as the song rolls on, we catch small details of their day – a child swinging, a bell ringing – and we feel what they feel. If country music wasn’t existential before, it was now.

2 – Help Me Make It Through the Night

Like drinking, sex had also been a topic in country music songs for years, but for the most part, it was always veiled – hinted at here and there, sometimes hidden beneath double entendres, and nearly always under the guise of marriage (including cheating songs). The sexual revolution started moving into Nashville in the 1960s (songs like “The Pill” were pushing boundaries), but Kristofferson’s song takes things further. It’s romantic in feel, but it’s more about lust – specifically, out-of-wedlock lust (“I don’t care what’s right or wrong”) that may just last a single night (“let the devil take tomorrow”) – and it’s direct, immediate, and bare-bones honest. By the time you get to the end, though, you also understand it’s about loneliness and the human desire for companionship – and that, right there, makes it absolutely beautiful. (The video above is the version by Sammi Smith, which reached No. 1 on the country charts, crossed over to the pop Top 10, and even won a Grammy.)

3 – Why Me

As Kristofferson recounts in the video (above), this song came from a moment in church that he was in no way expecting – and took him fully by surprise. However it happened, we are blessed with one of his most impactful songs. Yes, it’s religious in tone – but that’s not really what it’s about, or why it resonates so strongly these many decades later. It’s a human song, about a flawed person who’s facing up to his imperfections. Which, perhaps, is what’s at the core of so many of Kristofferson’s songs.

4 – Lovin’ Her Was Easier (than Anything I’ll Ever Do Again)

Tender and simple, this song (from Kristofferson’s second album, The Silver-Tongued Devil and I) has a timeless feel that some have called ‘poetic simplicity.’ Unfolding at a natural pace and rolling from verse to chorus and back again with ease, it’s a love song that picks up on universal themes of longing and, when released, immediately connected with listeners across generations. Since fans had already heard “Help Me Make It Through the Night,” the lyrics (“waking in the morning to the feeling of her fingers on my skin”) didn’t feel so out of place anymore.

5 – For the Good Times

“For the Good Times” is another of Kristofferson’s most famous songs, written a couple years before it appeared on his debut album. First recorded by Bill Nash, and then turned into a massive hit by country legend Ray Price, the song in some ways bridged the gap between old Nashville and the new breed of songwriting that would soon overtake Music Row. It’s a song about lovers parting ways, but the emotions are presented in such a lovely, nonjudgemental way (“Lay your head upon my pillow/Hold your warm and tender body close to mine”) that the song is almost impossible not to connect with. Even the sadness at its core is tempered by lyrics that rise above petty differences (“Let’s just be glad we have this time to spend together”).

6 – Me and Bobby McGee

If Kristofferson had written this one song, and then just stopped – gone back to flying helicopters and mopping floors, or teaching at West Point – he’d still be a songwriting legend. I mean, listen to those lyrics: they’re about small details (“windshield wipers slapping time,” “dirty red bandana”), but they stand out, they shimmer, they move, they are alive. And then you get that chorus. As Jason Isbell wrote on Threads, “Nobody’s ever beaten ‘Freedom’s just another word for nothing left to lose.'”