How Many Times Has Willie Nelson Been Arrested?

Willie Nelson is known for a few things: classic country music; long hair that he often wears in braids; and smoking a whole lot of pot. The musician's affinity for the potent leaf began in 1981 when he suffered a collapsed lung while swimming in Hawaii. Immediately following the incident, Nelson threw away all of his Chesterfield cigarettes and rolled twenty joints to replace them, as he recalled in his 2021 memoir "Willie Nelson's Letters to America."

He has even said that marijuana saved his life. "I used to smoke two or three packs of cigarettes a day, and drink whatever there was there to drink," he said during a 2019 appearance on The Tonight Show with Jimmy Fallon (via YouTube), "and I had pneumonia four or five times, my lung collapsed, I almost died. So I said, 'Wait a minute. I ain't gettin' that high off them Chesterfields ... So I throwed [sic] out the cigarettes, rolled twenty joints ... and I haven't smoked a cigarette since."

Despite allegedly improving his physical health, Nelson's weed habit has gotten him into a fair amount of legal trouble. Here are the details on the country musician's reefer-related, international criminal record.

Willie Nelson's first marijuana charge came in Dallas, Texas, in 1974 — five years before he fully swapped his cigarettes for joints, as noted by Wide Open Country. Three years later, in 1977, Nelson traveled to the Bahamas, where he was caught with weed in his jeans and jailed there. He allegedly snuck a six-pack of beer into his jail cell and had to be hospitalized for drunkenness upon his release hours later. He was then banned from the country, but the charges were dropped. His friend, President Jimmy Carter, reportedly congratulated him on getting out of trouble.

Nelson managed to keep a low profile throughout the '80s but was busted again in 1994, when police pulled him over and spotted a joint in his ashtray after an all-night poker game in Waco, Texas. He was pulled over again in 2006 while on his way to former Governor of Texas Ann Richards' funeral. The police found 1.5 pounds of marijuana and three ounces of hallucinogenic mushrooms on his tour bus, and he was sentenced to six months of probation.

Willie Nelson's most recent drug bust came in 2010 when the country singer was 77 years old. He was stopped in Sierra Blanca, Texas, near the Mexican border, by the notoriously strict Hudspeth County Sheriff Arvin West, who found six ounces of marijuana on Nelson's tour bus, per Wide Open Country.

"I had been in California hanging out for a while, and my bus had come out to pick me up because we had a couple of tour dates to do," Nelson recalled during an interview for Rolling Stone the following year. "I had forgotten that there was this little bag of weed on the bus that had been in the back there for weeks when I had been gone ... Naturally when they stopped us there the dogs came on and the first thing they went to was that little bag of pot back there." Nelson was briefly jailed before posting the $2,500 bail.

When discussing Willie Nelson's sentence for his 2010 drug bust, prosecutor Kit Bramblett notoriously joked that he would let Nelson off if he sang one of his songs in court. Nelson ended up paying a $500 fine to avoid a two-year jail sentence, per Wide Open Country.

Judge Becky Dean-Walker later rejected Nelson's prior agreement with the prosecution and reopened the case before her retirement in 2012. The case remains open ten years later. "If that was the guy on the corner, you can damn sure bet he would be charged with a felony," Dean-Walker told a journalist in 2011 (via Texas Monthly). "I don't have anything against Willie Nelson; I just think that it's not fair."

To a certain extent, Nelson agreed with the judge. "Every time we got busted, something good came out of it," he wrote in "Willie Nelson's Letters to America," adding, "Across our nation, there was more awareness and then resistance to long and unjust jail sentences. Not everyone gets to sing their way out of possessing a few joints. Over the years, Black Americans have been four times more likely to get arrested than their white neighbors. White or Black, those sentences destroy lives and families, and it costs tax dollars to lock people up for nonviolent crimes ... I believe that within a decade, medicinal and recreational marijuana will be legal in all fifty states."