Few artists are as readily associated with marijuana as country crooner Willie Nelson. In terms of identifiable pieces of the man, Nelson’s love of weed is right up there with the song “On The Road Again,” his long, braided locks, and his old, beat-up guitar, Trigger. But Nelson’s pro-pot advocacy wasn’t always something he pinned to his sleeve. Instead, his public affair with marijuana came about much like his career in the spotlight: Entirely on his own terms. When Nelson first started out, the world of country music was drilled down deep into the center of Nashville, Tennessee and mired in tradition. The audience was largely conservative, and as a result, Nelson went along to get along, presenting himself as a buttoned-down Western crooner with a knack for writing songs that had peculiar phrasing, which gave him a signature sound but not a standout look or personality. Eventually, Nelson wouldn’t so much find his niche as make it himself, writing songs that took a new and confident approach to the long-standing traditions of country music. As far as his personal habits, he was a known smoker for many years — and he has the arrest record to prove it — but over time Nelson would become one of the most renowned and outspoken advocates for marijuana legalization. Here’s a look at how Willie Nelson ended up transforming, not just the sound of country music, but the culture as well.

The Nashville Machine Even back in Nelson’s crisp white shirt days, he’d always fancied himself a smoker. Growing up in the small town of Abbott, Texas, he told GQ that there was nothing to do there but “f*ck, fight, and throw rocks.” To alleviate the boredom, Nelson took to smoking “anything you could roll up,” which included everything from lawn clippings to tree bark. He first tried pot when he was 11 or 12 while hanging out with his cousin. “He had asthma, and the doctors gave him a cigarette to smoke. An asthma cigarette. And he offered me a puff off it, and I didn’t particularly care for it so I handed it back to him.” A decade went by before he first tried pot again, this time when starting out as a country singer in the early 1950s. He told Cannabist that he was playing at a club in Fort Worth, Texas, and, like many of us, simply “ran into a guy who smoked pot.” Nelson, already a veteran smoker by then, started to incorporate pot into his routine, but admits that he went a “long time without getting high — for months I would smoke and smoke and I wasn’t getting high, and I couldn’t figure out why.” He eventually blamed the poor state of his lungs for keeping the true bliss of this fresh relationship at bay. Nelson stuck with it, though, and eventually had his eureka moment. In his 2015 memoir It’s A Long Story, Nelson admits that he dealt with a bit of a stigma as a marijuana user in the clean-cut world of country music, but never opted to quit outright, explaining that he “couldn’t betray marijuana any more than I could betray a family member or lifelong friend.”

Nelson, it turns out, was used to being an outsider. He moved to Nashville in 1960 where he soon got a job as a songwriter and famously penned hits like Patsy Cline’s “Crazy” and Ray Price’s “Night Life.” But while the chord progressions he’d write out on the page would deviate from convention, his style on stage was practically abstract art. He’d sing just off the beat, either a little ahead or a little behind, which proved to be too off-putting to country music fans, most of whom were steeped in decades of tradition. As the mecca of traditional country music, the Nashville sound was (and is) categorized by slick-sounding productions delivered in a more conventional style. Between his musical leanings and casual marijuana use, Nelson didn’t feel like Nashville was a natural fit and returned to his home state of Texas in 1970. Despite having his song “I’m A Memory” crack the top 30 the following year, Nelson was frustrated to the point that he quit music altogether.

Finding His Voice, His Audience, And His Home It wasn’t until 1972, when he discovered Austin — at the time, a sleepy college town known for its laid-back attitude and low-key party atmosphere — that he felt right. There, he didn’t feel the creative limitations that Nashville tried to force down his throat and he soon found an audience for his unique brand of country music that was tinged with jazz, blues, and gospel. It was there that he was able to come into his own by putting out some of the most memorable songs of his career; a period that would lay the foundation for the birth of outlaw country. As Nelson explained to the The Guardian in 2012, he saw Austin as a place to write and perform the songs he wanted to. Finally, he would be able to do it all his own way. “I saw hippies and rednecks drinking beer together and smoking dope together and having a good time together and I knew it was possible to get all groups of people together — long hair, short hair, no hair — and music would bring them together.” By 1974, Nelson had his first No. 1 hit with “Blue Eyes Crying In The Rain.” He’d also grown out his shaggy hair and beard and kept up his outlaw persona, racking up his first marijuana arrest when he was busted for possession in Dallas — first of many he’d experience over the years. Nelson’s arrest in Dallas began what would become a very public reputation with marijuana, one that even followed him to the White House back in 1976 when he was invited by then-President Jimmy Carter to thank him for all the work on his campaign. Nelson later revealed that he smoked a joint on the White House roof that night, but for years he remained coy about who he smoked it with. Turns out he’s mostly certain that it was Chip Carter, Jimmy Carter’s middle child.

Sill, marijuana had become far more than a way to collect wild anecdotes, as Nelson has flatly stated that he “would have been dead if it hadn’t been for pot.” He always had a bad temper, something he blames on his red hair, but he explained that drinking always made it worse. “When I was out in the bars drinking and fighting I was a little bit less of a peacemaker than I would be if I’d had a couple hits of a joint and gone and laid down somewhere. I’d have less bumps on my head, that’s for sure.” While he’ll still take a drink on occasion, Nelson replaced booze with pot, something he’d eventually do with cigarettes after his lung collapsed while he was swimming in Hawaii back in 1981. After he was hospitalized, he knew that he had to quit one or the other, and told NPR in 2012 that he simply “took a pack of Chesterfields and took all the Chesterfields out, rolled up 20 big fat ones and put [them] in there, and I haven’t smoked a cigarette since then.” Before long, all of Nelson’s vices were replaced with marijuana, writing in his memoir that “unlike booze, it had never made me nasty or violent. Unlike cocaine, it never sped me up or fired up my ego.” He refers to his use of the drug as something that started as a “love affair” and eventually “turned into a long-term marriage.”

Advocacy And Influence Nelson’s relationship with marijuana has become more than a running gag for the last several years. As an outspoken advocate of its legalization, he became one of the first celebrities to publicly address it. As Nelson states early on in the above clip from 2010, he saw the legalization of weed as an inevitability, albeit one that would take not only patience but the right combination of circumstances. That same year, nearly a dozen states had already legalized the drug for medicinal use, and with each passing year, more and more states have changed their laws. In 2012, Colorado and Washington both voted to legalize its use recreationally, without a medical prerequisite, which would’ve been unthinkable a few years earlier. While no one can single-handedly spark up a movement, it’s clear that the cultural acceptance gained by Nelson’s free embrace (despite the occasional legal dustup) had an effect on a burgeoning movement to legalize or at least decriminalize marijuana across the country. One that has turned conservative bastions like Nelson’s home state of Texas into a place where medicinal weed is now legal and there is talk about going even further in the future. Of course, this isn’t just about the embrace of pot as an artistic or lifestyle choice, it’s about the cold feel of a law pushing down on something it doesn’t understand, despite the proven benefits that range from helping with anxiety to enriching the lives of those suffering from cancer (and that’s to say nothing of the possible economic effect). Even Nelson himself, who is in large part the face of legalization, has admitted for years that he uses marijuana to simply help him deal with stress, and that if more people followed his lead, “It would make us get along better — all over the world.”