20 Things You Don't Know About Willie Nelson's Success Story

Willie Nelson's beloved by everyone from the Hells Angels to grandmothers. Here’s how he became an icon.

On The Road with Willie Nelson: 20 Facts About the Red Headed Stranger's Trailblazing Career

Sometimes lost in the fog of pot jokes about the world's most famous celebrity stoner is the fact Willie Nelson is a genius of popular American music — a bonafide living legend. Now in his 90th year, the pony-tailed "red-headed stranger" from Texas has been around so long that he's written more than 2,500 songs, lodged 60 hits on the country top-40 charts and sold more than 40 million albums.

The secret to Willie's success? He crafts seemingly simple songs that tap universal themes and resonate with, well, everyone. And then there's Willie's singing — a nasally, unmistakable quaver that he phrases not like a hillbilly, but a jazz singer. In a 2014 interview, Nelson's harmonica player Mickey Raphael perfectly characterized the scope of Willie's fan base this way: "The Hells Angels love him, and so do grandmothers."

Willie's been called a "hippie's hippie and a redneck's redneck." And it's paid off in a Forbes-estimated net worth of $25 million. Saddle up for a ride through Willie's epic career. At the end of the dusty trail, all he asks is you roll him up and smoke him when he dies.

He Wrote His First Song at Age Seven

Young Willie — Willie Nelson in the 1949 Abbott High School yearbook, when he was a junior.

Growing up in Abbott, Texas during the Great Depression, Nelson's grandfather bought him a guitar at age six. He learned a few chords, and a year later wrote his first song.

In a 2004 interview with "Rolling Stone", Nelson offered a sample lyric: "They took a gold star away from me when you left me for another, long ago." Nelson joked that as a seven-year-old "I'd never been left by anybody, so it was kind of funny."

Airman Nelson Reporting For Duty, Sir!

The last you'd expect of a pot-toking, pony-tailed peacenik like Willie is enlisting in the military. Yet after graduating high school in 1950, joining the U.S. Air Force is exactly what he did.

Willie's stint at Lackland Air Force Base in San Antonio, Texas lasted only nine months, at which point he received a medical discharge due to a bad back. But Willie hasn't forgotten his military roots and has long advocated for homeless veterans.

His Resume's Packed With Odd Jobs

Before Nelson's music career took off in the late 1950s, he wrangled a bunch of random gigs to help pay the bills. As a child, he picked cotton alongside his grandmother.

Later, Willie took turns as a tree trimmer, telephone operator, nightclub bouncer, pawn shop worker, saddle maker, dishwasher, radio disc jockey, and even a door-to-door salesman peddling Bibles, vacuum cleaners and encyclopedias.

His Recording Career Began in...Vancouver, Washington?

In 1957, working as a disc jockey at KVAN in Vancouver (just north of the Oregon border), Nelson wrote, recorded and marketed his first 45 rpm vinyl record entirely himself. There was no such thing as Kickstarter when Willie scraped together his own cash, had a Texas record company press 500 copies of his debut single, "No Place for Me," and hawked them on his radio show.

In a 1996 interview with NPR, Nelson remembers, "I sold them over the air, sold them an 8x10 picture and a record — I think both of them for a buck, which is about what it cost me to make it." The record was a minor, local hit and Willie wound up selling 3,000 copies.

"Hello Walls," Hello Money

In 1960, Nelson moved to Nashville, Tennessee with a few original songs in his pocket and hopes of hitting it big. Playing gigs and networking with fellow artists at a nightclub near the Grand Ole Opry, Willie got himself signed to a music publishing company and sold his song "Hello Walls" to country singer Faron Young, who scored a hit with the tune.

Nelson's first royalty check totaled $20,000 — a drop in the bucket compared to what the songwriter would earn for his ballad, "Crazy." Patsy Cline originally disliked the song, but her husband talked her into recording it, birthing what's arguably the most famous tear-in-your-beer jukebox song of all time.

Trivia: The song "Crazy" was originally titled "Stupid" (as in "I'm stupid for feeling so lonely"). But as a chuckling Nelson told Dan Rather in a 2016 interview, "Crazy was more euphonious."

He's Prolific

Willie Nelson in a top hat — Willie Nelson escorts Morgan Fairchild to the world premiere of their movie "Red Headed Stranger" in Austin, Texas, Feb. 1987.

Excluding live albums and greatest hits compilations, Nelson has cranked out an incredible 100 original studio albums, either solo or collaborating with other artists. His debut album "...And Then I Wrote" dropped in 1962 and contained a dozen originals, including "Crazy" and "Touch Me."

Over the next decade or so, Willie rode some ups and downs until hitting pay dirt with the blockbuster 1975 concept album "Red Headed Stranger." The LP spawned the hugely successful single, "Blue Eyes Crying in the Rain," and cemented Willie as a country superstar.

In '78, he struck gold again with the album, "Stardust," featuring covers of American standards like "Georgia on My Mind."

He's a Founding Father of ‘Outlaw Country’

While Nelson is considered a mainstream country legend, his actual music has often strayed far from commercial. In the '60s and early '70s, hangin' with the rebellious, hard-living likes of Johnny Cash and Waylon Jennings, the trio eschewed Nashville's radio-friendly sound and did their own thing — rooted in old-school Western swing, blues, rock, jazz and gospel.

The press branded the style "outlaw country." And from 1985 to '95, Nelson, Cash and Jennings, plus junior cohort Kris Kristofferson, cashed in big time when they formed the country supergroup The Highwaymen.

Dubbed "the Mount Rushmore of country music," the foursome released three albums, scored a hit single with "The Highwayman" and toured the world. In the must-see 2016 PBS documentary "The Highwaymen: Friends Till The End," Nelson calls the collaboration "some of the best times of my life."

Welcome to Willie World, Texas

Willie Nelson and his wife, Annie, arrive at the 2001 Grammy Awards in Los Angeles.

In Texas' Hill Country, some 30 miles west of Austin, the scent of weed wafts from what locals have dubbed "Willie World." Encompassing Nelson's 700-acre ranch and nearby properties, Willie's sphere includes a hilltop, log cabin-style home shared with his fourth wife, Annie. The ranch also includes Luck, Texas — an Old West town the singer had built as a set for his 1986 film "Red Headed Stranger."

Practically a golf tee-shot away from the ranch sits Nelson's personal recording studio; condos for his family and friends; and fanatical-duffer Willie's own nine-hole course, Pedernales Cut-N-Putt. Though it's open to the public and lacks a dress code, you must follow Willie's No. 1 course rule: "When another player is shooting, no player should talk, whistle, hum, clink coins, or pass gas."

He's Got His Own Radio Station

Pre-stardom, Willie disc jockeyed at radio stations in Texas and Washington. So it's fitting that today the red headed stranger stakes part-ownership in his namesake Sirius XM satellite radio station, Willie's Roadhouse (channel 61).

If you're after current chart-toppers by the likes of Luke Bryan and Keith Urban, look elsewhere. Willie's frequency spins country classics (think Hank, Waylon and Merle), features the weekly Grand Ole Opry broadcast, and airs the annual Farm Aid benefit concert.

His IRS Troubles Are Legendary

In Nelson's memoir "It's a Long Story: My Life," he recalls the early 1980s as a time when "tax shelters were being packaged and sold like corn dogs at the state fair." Unwisely, Willie bought into a few dogs and reckons that by the late '80s, his celebrity status and pro-pot stance helped make him a prime target for an IRS audit.

With Nelson's tax shelters deemed illegal and his early '80s tax deductions disallowed, by 1990 the IRS back taxes, penalties and interest piled up to some $32 million in government debt. Willie failed to pay and refused to file for bankruptcy.

His Fans Helped Bail Him Out

In an effort to pay his IRS tab while also poking fun at his problems, in '91 Nelson released the album "The IRS Tapes: Who'll Buy My Memories?" Fans snapped up copies to the tune of $3.6 million in sales.

Uncle Sam also seized and auctioned most of Nelson's assets. Again, fans came to the rescue, buying Willie's stuff — from cowboys hats to guitar amps — and donating it back to him.

Ultimately, Nelson sued his bookkeepers, Price Waterhouse, for doing him wrong over the years and won an out-of-court settlement for an undisclosed sum. By the mid-'90s, Willie had paid the IRS roughly $12.5 million, which satisfied his negotiated debt.

He Founded Farm Aid

Willie champions several causes, but perhaps the closest to his heart is the ongoing plight of America's family farmers.

At the 1985 Live Aid concert, Bob Dylan made on-stage comments about the mortgage crisis faced by U.S. farmers, inspiring Nelson to organize the first Farm Aid benefit later that year. The concert has been held nearly every year since and raised some $78 million to support family farm programs.

He's a Movie Star

Long before Willie began randomly appearing in comedy movies to smoke weed and crack jokes ("Half Baked," anyone?), he wasn't a half-bad actor in some decent pictures. Nelson's big-screen debut was a small part in the 1979 Robert Redford movie "The Electric Horseman."

A year later, he starred in his own vehicle (pictured), "Honeysuckle Rose." His best film might be 1982's oft-overlooked "Barbarosa," a gritty, compelling Western co-starring Gary Busey (before Busey became a punchline).

He Wrote ‘On The Road Again’ on an Airplane Barf Bag

In 1980, Nelson starred in "Honeysuckle Rose," a loosely autobiographical movie about life on the concert-touring road. In Nelson's book, "The Facts of Life and Other Dirty Jokes," Willie recalls an airline flight with the film's director and producer, who insisted the picture needed a new song about being on the road.

On the spot, Willie conjured the tune's enduring refrain about highway gypsies and making music with his friends. He remembers, "I said the words kinda bland I guess, maybe without any feeling or emotion. At the time, they were not that knocked out with the song. Of course, they couldn't hear the whole song like I could." Willie jotted the lyrics on an airplane-sickness bag, launching his signature song.

Music Runs in the Family

Though Nelson's recording and touring band is named "the Family," only one member is a blood relative. A piano player, Willie's older sister Bobbie Nelson joined his band in 1973 and has been backing her baby bro ever since.

In recent years, Willie's son Lukas Nelson (pictured, right) has made a name for himself fronting his own country-rock band, Promise of the Real — which also includes part-time member Micah Nelson, his younger brother. While POTR played as an opening act on papa Willie's tours, their big break didn't come 'till 2015 when Neil Young hired them as his main backing band. Then in 2018, Lukas co-wrote songs with Lady Gaga for the movie "A Star Is Born," and appeared in the flick with the band.

He Smokes Weed...Lots of Weed

Formerly a heavy whiskey drinker and cigarette smoker, Nelson often credits weed for saving his life. Though Willie puffed his first doobie in the mid-1950s, weed wasn't his 24/7 bag until around '78. The brutal booze hangovers swayed him to mostly put down the bottle. And since cigs don't get you high, Willie emptied his pack of Chesterfields and swapped them for twenty joints. He hasn't smoked tobacco since, and in a 2019 Rolling Stone interview said that nowadays he's stoned "pretty much all the time."

Nelson's wake-and-bake regimen astounds even Keith Richards, who in his 2010 memoir "Life," wrote, "Willie’s fantastic. He has a guy with a turned-over Frisbee, rolling, rolling, rolling. A beautiful weedhead is Willie. I mean straight out of bed. At least I wait ten minutes in the morning."

He Once Smoked Weed on the White House Roof

In a 2018 interview, Stephen Colbert asked Nelson if he'd like to smoke a joint with President Trump. Willie's prompt reply: "Oh yeah, he needs one bad. That could be good for him."

Chances are slim the President will extend Nelson a White House smoke-out invitation. But that's okay, Willie already enjoyed a 1600 Pennsylvania Avenue sleepover in 1977, hosted by his pal President Jimmy Carter.

Snoozing in the Lincoln Bedroom, Willie was awoken by the President's son, Chip Carter, who invited him for a toke. In a 2019 Rolling Stone interview, Willie remembers sharing a late-night, rooftop joint with Chip, who played tour guide and pointed out Washington D.C.'s monuments. Willie recalls, "It's really pretty nice up there." We assume he was referring to both the view and the high.

He's Got His Own Weed Company

In 2015, Nelson turned his pot devotion into a business venture with Willie's Reserve, which sells high-end cannabis strains grown by independent farmers sans pesticides. Available for sale in six states, Willie's brand also has non-traditional connoisseurs covered with edibles and vape gear.

What qualifies Willie as a cannabis purveyor? In a promo interview on the brand's website, Willie laughs and says, "I've spent enough time in jail, and I feel like I've bought enough of it, so I feel like I could be able to sell it to somebody."

His Guitar's Nearly as Legendary as He Is

Anyone even vaguely familiar with Nelson as a live performer has marveled at his battered acoustic guitar. The Martin N-20 nylon-string classical acoustic (pictured here in 2007) in Willie's hands is named "Trigger" (after Roy Rogers' horse) and was bought in 1969 sight-unseen for $750 from a Nashville guitar dealer. Trigger, covered in autographs by Willie's friends, has been by his side ever since. In the early 1990's, when the IRS seized Willie's assets, he even had his daughter hide the guitar at his home on Maui.

The hole worn through the front of Trigger, below the stings, has called for ongoing reinforcement of the guitar body. But after 50 years, it's still strumming strong. As Nelson is fond of joking, "I figure we'll give out about the same time."

He's Still Touring

The backstage craziness of Nelson's concert tours has dropped several notches since the 1970s, when his longtime tour bus driver Gator Moore says, "Everyone carried guns, everybody did drugs, everybody drank."

Nowadays, Nelson rides his plush, smoke-filled tour bus (nickname: "Honeysuckle Rose") to an average one-hundred gigs per year. He just celebrated his 90th at a star-studded Hollywood Bowl concert.

So, why's Nelson still at it? In his memoir "It's A Long Story: My Life," he writes, "The only money I've ever counted on is the money I make when you buy a ticket to my show. And if hearing my record on your laptop or your smartphone motivates you to come see me, I'm a happy man."