The Lesser-Known Truth Of Kris Kristofferson

The world lost a true American original on September 28, 2024 with the death of Kris Kristofferson, who passed away at age 88 at his home on the Hawaiian island of Maui. Born in Texas, Kristofferson went on to earn worldwide acclaim as a singer, songwriter, and actor, ultimately appearing in numerous films over the course of an extraordinary career that spanned from the 1960s until the 2020s.

Kristofferson was, in many ways, a walking contradiction; a highly educated scholar who was also a Golden Gloves boxer, an Army Ranger from a military background who turned down a prestigious military position that could have set himself up for life. In fact, he took a menial job as a janitor in a recording studio, emptying trash cans and fetching coffee, in order to place himself in close proximity with the music stars he so admired — stars who would, eventually, become not just his peers, but his ardent admirers. 

As fans remember his legacy and mourn his passing, there's no better time to read further and delve into the untold truth of Kris Kristofferson.

Kris Kristofferson grew up in a military family; his father, Lars Henry Kristofferson, was a major general in the U.S. Air Force, and his military career meant that the family moved frequently. When Kris was a teenager, the Kristoffersons eventually settled down in San Mateo, California. 

After graduating high school, Kristofferson attended Pomona College. It was there that Kristofferson flourished at creative writing, even winning a short story contest sponsored by the Atlantic Monthly thanks to the encouragement of two professors. "They both planted in me the idea of applying for a Rhodes scholarship," Kristofferson said of his writing professors in an interview with Pomona College Magazine. When the first round of interviews went poorly, the discouraged student told one of his profs, Dr. Frederick Sontag, that he was giving up — only to have Sontag spend hours convincing him to press on. "And I've been grateful to him ever since," Kristofferson added. He was awarded the scholarship and attended the prestigious Oxford University in the UK, studying English literature at the university's Merton College. He then went on to earn a master's degree. "It was one of the best things that ever happened to me," Kristofferson said of his experience as a Rhodes Scholar.

At that time, Kristofferson aspired to be a writer — not of songs, but of books. "I was going to write short stories and the great American novel," Kristofferson said when interviewed by radio host Studs Terkel, "but I haven't done it yet."

At Pomona College, Kris Kristofferson played several sports and excelled at all of them; in fact, before he set his sights on writing, he had a different goal. "I was going to be a boxer first," the former Golden Gloves boxer told Studs Terkel. He also played on the Pomona College football team. "I wasn't very big and I wasn't very fast," Kristofferson told the Pomona College Magazine, admitting he wasn't a natural at football; his professor, Dr. Frederick Sontag, recalled the words of football coach Jesse Cone, who told him, "Kris is a football player by the will of Kris Kristofferson, not by the will of God."

Kristofferson was also enthusiastic about rugby. He demonstrated so much athletic ability during his college years that he was featured in a 1958 issue of Sports Illustrated that highlighted his ability in all the sports in which he'd participated, while also pointing out that he'd been a long-distance runner in high school. Rugby, however, was a particular passion for Kristofferson; according to the website of Claremont Colleges Rugby, he was one of several students who, in 1957, was instrumental in reviving what was then known as the Pomona Rugby Club, which began in 1906 but faded away after World War II. 

While studying in Britain, Kristofferson continued his athletic pursuits, becoming a member of both the rugby and boxing teams. He was ultimately awarded The Blue — Oxford's highest student honor for athletics — for boxing.

After graduating from Oxford, Kris Kristofferson's family expected him to enlist in the military. He fulfilled that obligation; having participated in ROTC while attending Pomona College, he joined the U.S. Army as a captain. He followed in the footsteps of his father — a pilot — when he completed his flight instruction and became a helicopter pilot. He followed that up with the successful completion of Ranger School, arguably the most physically grueling program in the U.S. military. As an elite Army Ranger during the early 1960s, Kristofferson was stationed overseas with the 8th Infantry Division in West Germany. During that time, he formed a band and began writing songs, something he became increasingly passionate about.

After returning stateside, Kristofferson was offered a professorship to teach English at West Point. However, two weeks before he was supposed to begin, Kristofferson took a trip to Nashville, which convinced him to pursue his dream of becoming a songwriter. He turned down the job and remained in Music City, eventually landing a job as a janitor at Columbia Records in Nashville, where he hung around in hopes of breaking into the music biz. While emptying ashtrays in the recording studios, Kristofferson had the opportunity to watch some of country music's top musicians at work, up close and personal. 

Suffice to say, his parents were furious, and they essentially disowned him. "They thought that somewhere between Oxford and the Army I had gone crazy," Kristofferson told Pomona College Magazine. "And being virtually disowned was kind of liberating for me, because I had nothing to lose."

Kris Kristofferson's ability to pilot a helicopter resulted in one of his most memorable exploits. Though the feat took place before he rocketed to stardom, it ultimately proved instrumental in getting him there. 

While trying to launch himself as a songwriter in Nashville, Kristofferson had sent his demos to Johnny Cash in the hopes that the country music superstar would record one of them. When Cash expressed zero interest, legend has it that Kristofferson — who then had a side gig flying helicopters for a Louisiana-based company — decided to get the singer's attention by stealing a chopper and landing it on Cash's lawn. "Well, I admit that did happen," Kristofferson told Cowboys & Indians. "I think [Cash] told the story that I got out of the helicopter with a beer in one hand and a tape in the other. But he wasn't even in the house. And I never would have been drinking while flying a helicopter."

He also refuted the account of Cash's wife, June Carter Cash, who'd once claimed that when she saw the helicopter coming down her first thought was that it was the FBI coming to take her husband into custody. "She wasn't there either," Kristofferson recalled. "But you know what? I never was going to contradict either one of them." Despite his absence, Cash did find out about Kristofferson's stunt — and eventually hit No. 1 with his recording of the Kristofferson-penned "Sunday Mornin' Comin' Down."

Johnny Cash wasn't the first artist to record Kris Kristofferson's "Sunday Morning Comin' Down." Ray Stevens recorded it in 1969, but his version didn't make an impact. The following year, however, Cash's version catapulted to the top of the country charts and wound up winning song of the year at the CMA Awards.  

As successful as Kris Kristofferson became as a singer and songwriter in his own right, his songs also became big hits for other artists — often becoming even more successful than his own versions. That was certainly the case with "Me and Bobby McGee," which became a huge hit — albeit, sadly, posthumously — for Janis Joplin. As Kristofferson said in a 2012 interview with Tinnitist, her recording of "Bobby McGee" remains his favorite of all his songs that have been recorded by others. "But that's mainly because of my relationship with her," he said of the late singer, with whom he'd had a brief romance. 

Other artists to have hits with Kristofferson's songs include country singers Ray Price ("For the Good Times"), Waylon Jennings ("The Taker"), Carly Simon ("I've Got to Have You"), and Sammi Smith, who topped the charts with her recording of his composition, "Help Me Make It Through the Night." That song has also been recorded by such diverse artists as Willie Nelson, Gladys Knight & the Pips, and Michael Bublé.

When it comes to songwriting, regardless of musical genre, few artists have been as prolific and successful as outlaw country legend Willie Nelson. Having written such iconic tunes as "Crazy" and "On the Road Again" (and so many others!), Nelson knows a thing or two about writing hits. 

Interviewed by former Van Halen frontman Sammy Hagar for his "Rock & Roll Road Trip" TV show, Nelson admitted that as good a songwriter as he is, Kris Kristofferson was even better. Asked to single out "the greatest songwriter who ever lived," Nelson offered a short list of names that popped into his head, starting with Merle Haggard and Hank Williams. "And then you start guessing," he continued. "You got Kris Kristofferson, and Billy Joe Shaver, you know, and then you start running out of names."

Meanwhile, Kristofferson was both hero and mentor to Nelson's son, Lukas Nelson. "Kris helped me to believe in myself as a songwriter when I was a boy," Nelson, leader of the band Promise of the Real, wrote in a tribute on Instagram accompanied by a photo of Kristofferson holding Nelson when he was an infant. "Other than my father, he was my greatest inspiration ... He was a great among greats. One of the coolest men in music."

Kris Kristofferson had barely launched himself as a singer and songwriter — his debut album was released in 1970 — when he was offered a movie role, the bit part of "minstrel wrangler" in director Dennis Hopper's 1971 film "The Last Movie." "I didn't have a lot of acting in it, there was just like, one line at the beginning of the film ... I'd never been in a film before," Kristofferson told The AV Club.

That led to a larger role, and Kristofferson co-starred with Karen Black and Gene Hackman in "Cisco Pike" that same year. In 1973, Kristofferson got star billing alongside James Coburn and fellow musician Bob Dylan in Sam Peckinpah's western, "Pat Garrett and Billy the Kid," and the following year he shared the screen with Ellen Burstyn in the Martin Scorsese-directed "Alice Doesn't Live Here Anymore." Suddenly, Kristofferson had catapulted from country-rock star to matinee idol; other films included the Barbra Streisand-starring "A Star Is Born" (1976), the NFL-themed comedy "Semi-Tough" (1977) with Burt Reynolds, and the epic (and ultimately disastrous) western "Heaven's Gate" (1980).

As the years progressed, Kristofferson's Hollywood career ran parallel to his music career. Among his later hits were "Blade" and its sequels (playing a wily vampire slayer), and Tim Burton's 2001 remake of "Planet of the Apes." As he told The AV Club, the latter film didn't leave much of an impression on him. "I was a caveman type of guy. I think," he said of his role, adding, "It's not really an acting job. It's you more or less having to hit your mark."

All these decades later, the movie most associated with Kris Kristofferson is "A Star Is Born," in which he famously co-starred with singer/actor/director Barbra Streisand. However, Kristofferson wasn't Streisand's first choice to co-star in the 1976 remake. Streisand — one of the film's producers — envisioned the role of washed-up singer John Norman Howard as a comeback vehicle for Elvis Presley, whose movie career had long since fizzled out. Presley met with Streisand about the project, and was reportedly thrilled by the prospect of returning to the silver screen alongside her. 

However, those plans went south after Presley's manager, Col. Tom Parker, became involved. When the studio offered Presley $500,000 plus 10% of the film's net profits, Parker countered with a ridiculous demand: doubling Presley's salary to $1 million, along with 50% of the gross profits, and an additional $100,000 in expenses. The studio balked, and the deal was dead. That opened the door for Kristofferson, who eagerly stepped in. 

Ultimately, Kristofferson received acclaim for the role, even if he wasn't the original choice. He and Streisand both won Golden Globes, among the five "A Star Is Born" received; and, tragically, within months of the film's release, Presley was dead at the age of 42.

In 1984, Johnny Cash was set to film a TV Christmas special in Switzerland when he invited three fellow stars to share the stage with him. The result of this impromptu invite was The Highwaymen, a legendary country music supergroup featuring Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson. As Cash's daughter, Rosanne Cash, told Rolling Stone, the partnership was organic. "It came out of pure friendship," she told Rolling Stone. "There was no marketing guy who came and said, 'This will be a good idea.' My dad and Waylon were roommates in the Sixties, hiding their drugs from each other. Kris is like his little brother for decades ... They were all buddies and they wanted to do it."

Between 1985 and 1995, Kristofferson and the other members of the quartet recorded three albums, supporting the albums with concert tours. The four also starred together in a 1996 film, "Stagecoach." 

"Those tours and the records we made were a great time," Kristofferson recalled in a 2010 interview with Classic Rock (via Deadline), marveling at the experience of sharing the stage with the artists he'd first encountered when he was a janitor in their recording studio. "Hell, I was up there and I had all my heroes with me," Kristofferson said. "These are guys whose ashtrays I used to clean. I'm kinda amazed I wasn't more amazed."

Kris Kristofferson was the father of eight children, some of whom have followed their dad into the entertainment business, while others have preferred to stay out of the spotlight. However, it's fair to say that Kristofferson's son Jody embarked on a singularly unique path when he decided to pursue a career as a professional wrestler. 

Crafting a variety of names — including Jody Ray Kristofferson, Garrett Dylan (perhaps a nod to his dad's role in the film "Pat Garrett and Billy the Kid," in which he co-starred with Bob Dylan), and War Pig Jody — Jody Kristofferson wrestled for the WWE and other smaller operations. 

Speaking with Tinnitist, Kris Kristofferson exuded nothing but pride about the path that his son had chosen. "I identify with him so much, because people thought I was just as crazy as he is when I decided I was going to Nashville," Kristofferson explained. "But he loves it and he's committed to it just like I was with songwriting. And to be able to do what you love to do — you can't get better than that."

Throughout his 70s, Kris Kristofferson found himself becoming increasingly forgetful, and as his memory loss escalated, he feared the onset of Alzheimer's disease. Kristofferson responded to his fears in his own fashion: by writing a song about what he was going through. "I see an empty chair/ Someone was sitting there," read the lyrics to the unfinished song, as reported by Rolling Stone. "I've got a feeling it was me/ And I see a glass of wine/ I'm pretty sure it's mine."

Kristofferson was prescribed medication for Alzheimer's and depression, but everything changed when doctors discovered he'd been misdiagnosed; his symptoms were the result of Lyme disease, not Alzheimer's. 

Once he began being treated for Lyme disease, the fogginess he'd been battling for years miraculously and quickly lifted. "Kris is as sharp as he's been in the past 20 years because of his treatments," a friend told Closer Weekly in 2016.

At the ripe old age of 84, Kris Kristofferson decided it was time to pack it in. While most artists of his stature would unveil the news of retirement in an official announcement, or possibly even ride off into the sunset with one final farewell tour, Kristofferson took a far more low-key approach by simply stepping back and telling no one.

After a while, though, his absence from the spotlight was noticed. In 2021, his management confirmed that he'd retired. According to Kristofferson's manager, Tamara Saviano, he hadn't actually planned on retiring until the COVID-19 pandemic shut down all live music performances. "It wasn't any big stake in the ground, like 'I'm retiring! I'm not doing this anymore!'" she told Variety. "It was an evolution, and it just felt very organic ... Kris is 84. It didn't feel like such big news to us. That's why there was no announcement: It was just sort of a slow changing of the guard thing."

At the time, Saviano insisted the term "retirement" was being used somewhat loosely. "It doesn't feel like a retirement because Kris' music isn't going anywhere," she explained. "There are still going to be new projects ... But he's not going to be on the road anymore."