IIn 2009, actor Ethan Hawke wrote a profile of Kris Kristofferson for Rolling Stone magazine. It’s an intimate, revealing interview that spans from the Grand Ole Opry to Heaven’s Gate and runs several thousand words. In truth, it could be summed up in a single sentence: “Kris Kristofferson is made of thicker and more complicated stuff than most celebrities today.”

Kristofferson’s life was quite remarkable: An Oxford-educated Army captain who gave up his military career to pursue music in Nashville, he won four Grammys, moved into acting, worked with Sam Peckinpah and Martin Scorsese, and won a Golden Globe. His songs have been performed by everyone from Johnny Cash to Janis Joplin, Al Green to Gladys Knight. At 40, he formed a chart-topping outlaw country supergroup with Cash, Waylon Jennings and Willie Nelson. He continued to record and perform into his 80s.

Over time, he would come to represent a particular brand of American masculinity; undeniably unconventional and intellectual, but also harsh and defiant. A soldier who studied English literature; a lover of Hank Williams and William Blake; A songwriter who is able to come up with the lyrics to “Me and Bobby McGee” while sitting on an oil rig off the coast of Louisiana. “Something inside me made me want to do the hard things,” he once said. “Part of it was that I wanted to be a writer and I realized I had to get out and live.”

Certainly things would have been much easier for Kristofferson if he had taken the job as an Army instructor instead of pursuing his Nashville dream. The closest he came to a music career was for several years when he worked as a janitor at Columbia Studios. On weekends he made a little money flying helicopters for offshore oil rigs in the Gulf of Mexico.

He was determined to become a songwriter; otherwise, a novelist. But these wishes were often in conflict with the responsibility towards a woman and a young family. He drank heavily, dressed shabbily, and after a while his parents—upstanding military types who had little interest in country music—decided to disown him by letter. “No one over 14 listens to this kind of music,” his mother wrote, “and if they did, they wouldn’t be someone we want to know.”

In 1969, he divorced and lost his job on the oil rigs because of his drinking. But after a while in the depths of his soul, Kristofferson’s life took an upward turn: three of his songs were recorded by rising country star Roger Miller, along with covers by Bobby Bare, Sammi Smith, Ray Price and others.

Later that year, after many attempts, Kristofferson finally caught the attention of his hero Johnny Cash by landing a helicopter in the star’s yard and strutting out of the pilot’s seat with a demo cassette in one hand and (Cash claimed) a beer in it others. On the tape was a recording of the song Sunday Mornin’ Comin’ Down. Cash was struck. The track debuted at No. 1 and was named Song of the Year by the Country Music Association.

The first song Kristofferson ever wrote was a pro-Vietnam tune, which he later regretted. Over the course of his career, he has atoned for the misstep in a number of activist songs, including Bobby Bare’s 1969 recording “The Law is for the Protection of the People,” 1986’s “What About Me,” which excoriated right-wing hostility to the military Central America questioned, and 2006’s “Anti” war anthem in the news.

Sometimes, and in certain circles, political attitudes made the rise of his career somewhat steeper. “After giving concerts for the Palestinian children, I noticed a significant lack of work… and if it has to be this way, it has to be this way,” he once said. “If you support human rights, you have to support them everywhere.” In 1992, he famously expressed solidarity with singer Sinéad O’Connor, who had left the Saturday Night Live audience horrified when she displayed a picture of the Pope in protest against the Catholic Church John Paul II tore up. Soon after, Kristofferson took the stage at a Bob Dylan anniversary concert in New York City and put his arm around her as the audience booed: “Don’t let the bastards get you down,” he told her.

The Rolling Stone profile also begins with a political sparring match. Hawke remembers standing next to Kristofferson at a Willie Nelson tribute, where a major country music star admonished the singer to cut out the “left-wing shit” for the evening. Kristofferson reins in and tells the upstart to heel. “Have you ever served your country?” he asks him. “The answer is no, you didn’t. Have you ever killed another man? Huh? Have you ever taken another man’s life and then cashed the check your country gave you for it? No, you didn’t. So shut the fuck up!”

As much as his strong political positions fueled Kristofferson’s reputation as an outlaw, they also fueled his songwriting, establishing his guiding themes of fairness, freedom and desire, and bringing into focus something that was steadfast and unshakable and that might at a glance look like toughness . and in another it might seem something like hope. His first publisher, Marijohn Wilkin, noted in a 2003 interview with Nashville Scene that Kristofferson’s songs were initially too long, too perfect, and limited by neat grammar. He had to work to find their grain.

What he developed was a songwriting style based on the tension between this harshness and a deep sensuality. It’s there in the untied headband of Help Me Make It Through the Night and the fried chicken of Sunday Mornin’ Comin’ Down, in the quiet, human desolation that runs through so many of his lyrics.

Play Kristofferson’s version of “Me and Bobby McGee” and you’ll hear it there too: how it becomes a song based not so much on the vocals but on the verses, played slower, more swinging in its setting and can be sung with a gentle resignation. “Freedom is just another word for nothing to lose,” he sings like someone who knows the taste of both; In his hands the song somehow became thicker and more complicated.