10 Of The Most Insane Willie Nelson Career Stories

Willie Nelson is more than just a legendary country singer—he’s an American icon. Known for his outlaw spirit and incredible musical talent, Willie’s life is packed with stories beyond music. Here are 10 of the most insane Willie Nelson career moments you may not know about:

He Penned His First Song at Just Seven Years Old
While most kids were still figuring out how to color inside the lines, Willie Nelson was writing songs. He started composing music at just seven years old, and one of his first songs was inspired by his music lessons with his grandmother. Willie told Rolling Stone in 2004: “We’d get a gold star if we did well. So, I wrote a song about it—‘They took a gold star away from me when you left me for another, long ago.’ I’d never been left by anybody, so it was kind of funny.” Even as a kid, Willie had a way with words.

He Used to Sell Bibles
Before he became a full-time musician, Willie Nelson worked several odd jobs, including selling Bibles door-to-door. Growing up in Texas, he worked as a cotton picker, a disc jockey, and whatever else he could find to make ends meet. It wasn’t until the mid-1950s that Willie decided to go all-in on his music career—and the rest, as they say, is history.

He Ran Into a Burning House… to Save His Pot
In 1980, Willie came home to find his house in Nashville on fire. Most people would grab family photos or important documents, but not Willie. “By the time I got there it was burning real good,” he told People magazine. “I had this pound of Colombian grass inside.” Willie rushed inside, not out of bravery, but to save his stash of marijuana. His hundred unreleased song tapes? Unfortunately, they didn’t make it out. Willie later joked, “I wasn’t being brave running in there to get my dope; I just didn’t want the firemen to find it!”

He “Retired” in 1972 But It Didn’t Last
In 1972, Willie Nelson was so fed up with the music business that he paid $14,000 to buy out his contract and retire to Austin, Texas. But Willie couldn’t stay away from music for long, especially with Austin’s vibrant music scene pulling him back. Within a year, he was back in action with Shotgun Willie, and soon after, he released some of his biggest albums, like Red Headed Stranger and The Troublemaker.

He’s Been Playing the Same Guitar for Over 50 Years
Willie’s trusty guitar, “Trigger,” has been by his side since 1969. Named after Roy Rogers’ horse, this well-worn Martin N-20 is as legendary as the man himself. Willie told Uncut Magazine in 2014, “I have to take good care of Trigger.” The guitar has so many autographs, signatures, and stories attached to it that it’s practically a piece of music history in its own right.

He Recorded an Album to Settle a $32 Million Tax Debt
In 1990, the IRS came knocking, and Willie found himself with a massive $32 million tax bill. The IRS seized most of his assets—everything except Trigger, his guitar. To help pay off the debt, Willie recorded The IRS Tapes: Who’ll Buy My Memories? and sold it via a 1-800 number. At least 15 cents of every dollar went straight to the IRS. It may not have been his favorite project, but it helped clear his debt and added another wild chapter to his life.

He Wrote a Famous Hit on a Vomit Bag
Willie’s famous hit “On the Road Again” was written in one of the most unexpected places—on an airplane vomit bag. During a flight, producers Sydney Pollack and Jerry Schatzberg asked him if he had any song ideas for their movie Honeysuckle Rose. Willie thought for a moment and then scribbled down, “On the road again, I can’t wait to get on the road again.” When they asked about the melody, Willie famously replied, “I don’t know yet.”

He Had a Duet With President Jimmy Carter’s Wife, Rosalynn
Willie has a long friendship with former President Jimmy Carter, and in 1980, he performed at the White House for the Carters. During the show, Willie sang a duet of “Up Against the Wall, Redneck Mother” with none other than First Lady Rosalynn Carter. In typical Willie fashion, he later recounted how he then went up to the White House roof and smoked a joint. The friendship continued, and in 2012, Willie and Carter even performed “Amazing Grace” together in Atlanta.

His Album Stardust Spent Years on the Charts
In 1978, Willie released Stardust, an album of pop standards like “Georgia on My Mind” and “Unchained Melody.” The album became a massive success, spending two years on the Billboard charts and a whopping 540 weeks on various country music charts. It remains one of his most beloved albums and proved Willie could conquer more than just country music.

He Found a Business in Cannabis
Willie Nelson has never been shy about his love for marijuana, and as legalization has spread across the U.S., he’s turned his passion into a business. He launched his own marijuana brand called “Willie’s Reserve,” which sells high-quality cannabis products in states where it’s legal. Willie’s not just a musician—he’s a weed-repreneur.