Like John and Yoko, Gable and Lombard, Pancho and Lefty, the love story of Willie Nelson and smoking weed is one for the ages. Yet it, too, seems to have met a tragic end. This week, Nelson told a reporter for San Antonio’s KSAT-TV that health issues have forced him to stop smoking marijuana, ending a decades-long relationship that, like the most passionate romances, still takes his breath away. Unfortunately, he meant that literally: years of abusing his lungs have left the 86-year-old country star with breathing problems, so he’s since quit smoking everything. Even his beloved pot.

While Nelson notably didn’t say he’s given up vaping, edibles, or any of the other myriad ways science has come up with to get you high, it’s hard to think of a more iconic power couple than Willie Nelson and a lit joint. Theirs was a love affair that lasted for more than 60 years, remaining steadfast throughout decades of shifting attitudes toward cannabis—and even inspiring some of those changes itself. In honor of Willie breaking up with smoking weed, let’s look back through some of the misty, bong-water-colored memories of the way they were.

1954: Willie and weed first meet

In his 1988 memoir, Willie: An Autobiography, Nelson wrote about the moment he first laid eyes on marijuana at a Fort Worth bar. Nelson had been watching the Joseph McCarthy hearings, he said, when local musician Fred Lockwood invited him to step outside and “blow tea.” Overcome with anxiety, he opted to take the joint home instead. While driving later that night, he gave in to temptation, pulled over, and smoked it, but he felt nothing. In fact, it would be another six months of dating before he and weed finally clicked. 

1970: Willie saves weed from a burning house

By the end of the sixties, Willie and weed were inseparable. In fact, when his Nashville house caught fire, Nelson ran back into the flames to save his guitar, Trigger, as well as a “pound of Colombian grass,” as he would later tell People—a desperate measure he says was motivated equally by not wanting to go to jail.

1971: Willie and weed move to Austin

After years of knocking around as a songwriter and session player, and growing dissatisfied with his own stagnant solo career, Nelson moved to Austin in 1971, where he found fresh inspiration in the psychedelic music scene, grew out his hair, and found the nexus between hippie and cowboy. Willie and weed were finally home. 

1974: Willie and weed have their first arrest

In 1974, Nelson had his maiden arrest for marijuana possession in Dallas, officially making his relationship with weed a matter of public record. The special occasion was immortalized in a now-classic mug shot that still adorns many a T-shirt.

1977: Willie and weed are kicked out of the Bahamas

During a 1977 tour, Nelson and songwriter Hank Cochran took some downtime in the Bahamas, but their vacation was waylaid after customs agents found Nelson’s weed stowed away inside of his jeans. Nelson escaped the charges, but the local law ordered him never to return, banishing him from paradise over his forbidden love. 

1978: Willie and weed go exclusive

As he recently recalled for Rolling Stone, Willie and weed finally settled down into blissful monogamy around 1978, when he finally gave up cigarettes and whiskey to commit himself fully to marijuana. “It saved my life, really,” Nelson gushed, crediting it with his long life, his sanity, and his overall happiness.   

1980: Willie takes weed onto the White House roof

In 1980, Nelson was invited to perform for President Jimmy Carter in the Rose Garden, and, as he explained to Rolling Stone, later that night, Carter’s son Chip invited him and his weed onto the rooftop overlooking D.C. There they burned what Nelson described in his autobiography as “a fat Austin torpedo,” a rendezvous that became at once an instant legend and easily the coolest thing to ever come out of the Carter administration. 

1994: Willie and weed miss the Grammys

Driving back to Austin exhausted after a late-night poker game in Hillsboro, Nelson pulled his Mercedes over on an I-35 frontage road near Hewitt to take a nap, only to be awakened by two highway patrolmen. After the cops discovered a joint in the ashtray and a baggie of weed stashed under the driver’s seat, Nelson was once again arrested, forcing him to cancel a scheduled appearance at the 1994 Grammys so he could be in court. Sure, lots of performers have skipped the Grammys over the years. But how many did it for love?

1998: Willie and weed co-star in Half Baked

In 1998, Willie and weed lit up the screen in Dave Chappelle’s stoner comedy Half Baked, with Nelson playing the “you shoulda been there smoker” who schools Chappelle on the good ol’ days. Theirs was an electric pairing, and Willie and weed would go on to appear in many more movies—The Dukes of Hazzard, Beerfest, Surfer, Dude—that cemented their on-screen chemistry.  

2000: Willie and weed broadcast their love on the radio

Nelson’s ardor took a decidedly political turn toward the millennium, with Nelson joining the advisory board for the National Organization for the Reform of Marijuana Laws (NORML). He also recorded a series of radio ads in which he spoke of how loving marijuana was only right and natural among consenting adults. 

2005: Willie and weed run afoul of the Texas GOP

Democratic Texas senator Gonzalo Barrientos introduced a bill in 2005 that would name a 49-mile section of Texas Highway 130 after Nelson, a proposal that had support from nearly all of his fellow lawmakers. But then, Republican senators Florence Shapiro and Jeff Wentworth objected, citing, in part, Nelson’s consorting with marijuana.

2006: Willie and weed miss Ann Richards’s funeral 

While driving from Louisiana to Texas to attend the funeral of Governor Ann Richards, Nelson was stopped in St. Parish and arrested for possession of both weed and hallucinogenic mushrooms. Nelson claimed the weed as his. (The mushrooms were just some meaningless fling.) He missed Richards’s funeral, and later canceled a series of concert dates to appear in court, where he received six months’ probation. 

2008: Willie and weed meet Snoop Dogg

After an almost-as-legendary session with Texas Monthly contributor Andy Langer, Willie and weed finally met up with rapper Snoop Dogg in Amsterdam, where Nelson proceeded to smoke Snoop under the table. The historic menage a trois blossomed into a fruitful shared romance over the years, with Nelson collaborating on both Snoop’s countrified 2008 track “My Medicine” and 2011’s “Superman,” as well as on countless more bongs. 

2010: Willie and weed are caught by the Border Patrol

Drug-sniffing dogs at the border near Sierra Blanca descended upon Nelson’s tour bus in 2010, leading to the discovery of six and one-quarter ounces of marijuana. Nelson’s subsequent arrest became something of a cause celebre after the prosecutor jokingly suggested he be let off with a small fine and a performance of “Blue Eyes Crying in the Rain” for the court—another knowingly meager punishment for the famed smoker that, as The New York Times pointed out, did more to “demonstrate the ineffectiveness of marijuana prohibition than a hundred lobbyists or a thousand politicians could ever do.” The moment also emboldened Nelson to create the Teapot Party, a political group advocating for the full legalization of marijuana that continues to draw supporters today.

2012: Willie and weed release “Roll Me Up And Smoke Me When I Die”

Capping off several decades of memorable duets, Willie and weed collaborated once again on the 2012 single “Roll Me Up and Smoke Me When I Die,” with fellow out-and-proud weed lovers Kris Kristofferson, Jamey Johnson, and Snoop Dogg all joining in. The song, later released on green-colored vinyl, made its debut just after 4:20 p.m. on April 20 in Austin, where Nelson performed it at the unveiling of a statue in his likeness.

2013: Willie and weed stand up for same-sex marriage

As the Supreme Court argued over the Defense of Marriage Act in 2013, Nelson gave an interview to Texas Monthly’s Andy Langer, in which he offered his own defense of a person’s right to love whomever or whatever they damn well please. Nelson posed with a placard depicting the familiar “equal sign” logo of the Human Rights Campaign, here replaced by two marijuana cigarettes.

2015: Willie and weed launch Willie’s Reserve

As a newly enlightened America finally began to shrug off the decades of bigotry (in certain states), Nelson announced the launch of Willie’s Reserve, his very own brand of marijuana and accompanying chain of stores. That venture has since grown to encompass everything from chocolates to coffee to CBD treats for pets, representing what his spokesman once called “a culmination of Willie’s vision, and his whole life.” While Nelson might have had to quit smoking weed, at least they’ll always have that, along with so many memories—whichever ones they can recall.