And that’s what country music is. We have some different things nowadays, you know, where guys dance and everything. And uh some of them are great, you know, and some of them are just imitators. Waylon Jennings was the kind of man who said exactly what he meant, did exactly what he believed, and never once apologized for either.
It’s freedom, you know, I I’ve never tried to change them and they’ve never tried to change me, He did not perform authenticity, he lived it. From the way he made music to the way he raised his family, to the way he walked into a room full of strangers and made every single one of them feel like they had known him for years.
This is a man who who who had something to offer the world. He was loyal to the people he loved, brutally honest with the people he did not, and completely unwilling to pretend to be anything other than what he was, even when it cost him everything, and it did cost him more than once. And I just wanted a little freedom. I didn’t want to sound like everybody else.
But what most people do not realize is that being exactly who he was also helped generate over 63 million dollars in humanitarian aid and played a role in saving millions of lives across an entire continent. He just had a heart as bigger than Texas. That is not an exaggeration and it is not a metaphor, it is what actually happened.
And the question that nobody seems to ask is how. How does a country singer from a small town in Texas end up changing the course of history just by refusing to be fake? That’s what you get for loving me. It started with five words he said to his best friend on a freezing night in Iowa. Five words that would haunt him for the next 43 years of his life.
You know, that cost me uh not ever getting involved or In 1958, a 21-year-old kid named Waylon Jennings was working as a radio DJ in Lubbock, Texas, playing records and talking into a microphone for a station that anyone barely listened to. He had no money, no connections, and absolutely no reason to believe that his life was about to change forever.
Buddy was what I call a nut. He would laugh all the time. Then one afternoon, Buddy Holly walked into the station, handed him an electric bass guitar, and said, “You have 2 weeks to learn to play that thing.” Holly was already a star, a genuine rock and roll sensation who had toured the world and played with legends.
And for reasons that Waylon himself never fully understood, Holly decided that this unknown kid from a tiny West Texas town was worth believing in. He took Waylon under his wing, produced his first recording session, bought him new clothes, and told him something that Waylon would carry with him for the rest of his life, “Don’t ever let people tell you you can’t do something, and never put limits on yourself.
” You get that rhythm and it don’t stop, you know, and don’t go anywhere but right. And I learned that about it and not to compromise your music. Years later, Waylon would say that Buddy was the first guy who had confidence in me, and that he had as much star quality as an old shoe, but Buddy really liked him and believed in him.
In January 1959, Holly put together a tour called the Winter Dance Party, a 24-city run through the frozen Midwest in the dead of winter, and he wanted Waylon on bass. The conditions were brutal from the very first night, with temperatures dropping to 35 below zero, and the tour bus breaking down so many times that the performers had to burn newspapers inside it just to keep from freezing to d.e.a.t.h .
People on there couldn’t get any rest, and you know, all our clothes were dirty. We were just smelled like billy goats. The drummer ended up in the hospital with frostbitten feet, and half the performers on the bus were sick. On the night of February 2nd, after a show at the Surf Ballroom in Clear Lake, Iowa, Holly had enough and chartered a small plane to fly to the next stop.
There were only three extra seats, and Waylon was supposed to be on that plane, but the Big Bopper, a 250-lb man who was suffering from the flu, asked Waylon if he could take his seat instead. Waylon gave it up without a second thought because the man was too sick to ride that bus any longer. When Holly found out, he leaned back in a chair and laughed, “So, you are not going with us tonight, huh? Well, I hope your old bus freezes up again.
” 19 years old, and I said, “Yeah, well, I hope your plane crashes.” They were joking, the way friends do when they have been on the road too long and everything feels like it will last forever. A few hours later, that plane went down in a frozen cornfield 6 miles from the airport, and Buddy Holly, Ritchie Valens, the Big Bopper, and the pilot were all killed instantly.
Waylon was on the bus when he found out, and the only word he ever used to describe that moment was numb. You’re never ready for someone dying, and when you feel like you feel guilty about it. He could not attend the funeral because the tour promoters forced the remaining performers to keep going, and for years afterward, he would not even pick up a guitar.
And I didn’t look I never even saw the a picture of the plane crash until 15 years later. His own son, Shooter, would later say that his father felt like he was on bonus time from that point forward, that he had to live with purpose because he survived. That was that was a turning point in my driving my life.
Something changed inside Waylon Jennings on that frozen night in Iowa. Something that would take years to fully reveal itself, but that would never go away. I heard later that Tommy and and Ritchie flipped coins. He would never again waste a single moment of the time he had been given, and he would never again stay quiet when something felt wrong.
Years later, there would come a night when that refusal to stay silent would matter more than anyone in the room could possibly imagine. But that night was still a long way off, and Waylon had a lot of living left to do before he got there. After years of grief and silence, Waylon eventually picked up the guitar again and moved to Nashville, Tennessee, expecting to find a music industry that valued the same things Buddy Holly had taught him, originality, honesty, and the freedom to make music that came from your gut instead of
a formula. I always said, “Why?” And why was not a welcome word in Nashville when when I came here. When I wanted to do something, they’d say they’d say, “Well, you can’t do that.” And I’d always say, “Why?” What he found instead was a machine that had no interest in originality. And me and the Nashville sound was like oil and water. It just didn’t mix.
There was no edge to that music. Nashville in the 1960s ran on a system where the label owned you, the producer controlled you, and the only thing anyone cared about was whether you could fit into the same polished, predictable sound that every other country singer was making. They would not let Waylon use his own band, they would not let him pick his own songs, and when they put him in the studio with a producer named Danny Davis, a man who rolled his eyes and made wise cracks every time Waylon tried to do something different, the tension
got so bad that Waylon showed up to the next recording session with a pistol he had borrowed from Merle Haggard and told the room that anybody still looking at their chart after the third take was going to have a problem. Is that a big gun, by the way, a bunch of It’s a long nose gun. Yeah.
And what you can’t hit nothing with it. [laughter] During one of his contract negotiations with RCA Records, the label was offering him almost nothing, and Waylon got so fed up that he stood up in the middle of the meeting and walked to the bathroom. I knew what they were doing here wasn’t right, and I knew it wasn’t fair, and not to somebody like Waylon who was a genius.
While he was gone, his manager let the silence do the talking, and by the time Waylon got back, the label had agreed to every one of his demands, including something that no country artist in Nashville had ever been given before, full creative control over his own records. His manager met him in the hallway and said, “That was a $25,000 piss.
” So, they tried to destroy me, and consequently in the process, they destroyed themselves. Once Waylon had control of his own music, everything changed. A songwriter named Billy Joe Shaver had been chasing him for months, trying to get Waylon to listen to his songs, and when Waylon kept dodging him, Shaver finally cornered him in a hallway and said, “If you don’t listen to these songs, I’m going to whip your right here in front of God and everybody.
” Waylon listened, and the result was Honky Tonk Heroes, the album that most historians consider the first true outlaw country record. In 1975, he won the CMA Award for Male Vocalist of the Year, and his acceptance speech became legendary. They told me to be nice. I don’t know what they meant by that. Thank you.
I GOT ONE THING TO SAY, WAYLON, it’s about damn time. By 1976, Waylon and Willie Nelson released Wanted: The Outlaws, the first country album in history to be certified platinum, and when he became the narrator of The Dukes of Hazzard, his voice became one of the most recognizable sounds in American television.
But what made Waylon different from every other rebel Nashville had ever seen was not just that he fought for himself, he fought for the people he believed in. When Columbia Records tried to add studio production to Willie Nelson’s stripped-down album, Red Headed Stranger, because they thought it sounded like a demo, Waylon was in the meeting and lost his mind, calling the label president a tone-deaf son of a and threatening to fire their shared manager if they touched a single note. Waylon and I were like two old
married people. We fought about everything. And if he was for it, I was against it, and of course he didn’t listen to me. He went on to Nashville and did great. The album was released exactly the way Willie recorded it and it went gold. And then there was the friendship that nobody in country music saw coming, Muhammad Ali.
Kris Kristofferson introduced them in 1978 and a country music outlaw from Texas and the most famous boxer on the planet became genuine friends, the kind of friends who show up for each other without being asked. When Waylon’s son Shooter was born, Ali came to the christening, sat down on the couch and announced with a grin, “I’m here to integrate this joint.
” He became Shooter’s godfather and the friendship lasted until the end. Authenticity does not care where you come from and it does not care what you look like. It only cares whether you mean what you say and both of those men always did. And one day, in a room full of people who were all too afraid to say what needed to be said, that authenticity was going to matter more than any hit record or platinum album ever could.
Just don’t compromise. That’s all I always said and do what you do. Well, you certainly don’t compromise. That’s for sure. Waylon Jennings once bragged that he never drank a drop of alcohol in his entire life and technically that was true. But what he left out was that he was spending $1,500 a day on cocaine while he said it.
I was on drugs for 21 years almost solid, you know. I like John, I had blackout times too but I remember most of it too. He later told an interviewer with the kind of honesty that only a man who has survived his own stupidity can deliver, that he would sit there stoned out of his gourd but feeling real proud of himself because at least he never touched a bottle.
At his peak, he was consuming 7 g a day, waking up at 3:00 in the morning for another line and hiding security bundles of cocaine in briefcases all over his house so he would never be caught without a stash. In 1977, the DEA showed up at the Nashville studio where he was recording and what happened next sounds like a scene from a movie that nobody would believe.
You become very uninhibited when you’re His drummer Richie Albright pressed the talkback button on the mixing board which sent the agents’ voices directly into Waylon’s headphones in the recording booth. And while Waylon bought time by pointing out that the arrest warrant had the wrong address on it, Albright grabbed the cocaine, shoved it down his pants, walked calmly to the bathroom and flushed every gram of it.
Was a trifle excessive? [laughter] OH MY GOD. THE charges were dropped and Waylon wrote a song about it. This song’s about the night they spent protecting you from me. But the drugs did not stop and neither did the consequences. You know, I kind of withdrew from everybody for several years, you know. I mean, when you’re Well, my mind was just about gone and I was you know He went bankrupt, owing two and a half million dollars, got booed off the stage in Portland after barely making it through a few songs and missed a White House lunch with President Carter
because he was too wired to show up. You know, you can always find excuses for taking drugs and sometime it was a a pain, a broken bone that I would take Mud Off My Shoulder. You know, I’d like to say that I sincerely thought that you would never amount to anything. [laughter] His wife Jessie later wrote that she loved his sincerity but could not abide his addiction and she spent years force-feeding him protein milkshakes just to keep him alive because cocaine had completely destroyed his ability to eat.
Then one day, Waylon walked into his house and found his 3-year-old son Shooter sitting on the floor with a cut-off straw pressed against his nostril, pretending to snort cocaine, pretending to be just like daddy. It was the single most devastating thing Waylon Jennings had ever seen and it still took him two more years to find the strength to quit.
But once he started getting clean, something else happened that finally sealed it because one afternoon Shooter came over and sat down beside him, put his little arm through his father’s arm and the two of them just sat there coloring together for over an hour without saying a word. Everybody that that cared about me I I when I sobered up, I was just going to quit for a month.
Waylon later said that was the first time his son had been able to do that because he had been so scattered all the time that a child could not even sit next to him. I got to looking around me and I saw my wife who’s a beautiful lady and but she looked like she was getting worse.
She looked like she was 10 years older because of the stress and strain of living with me. When he finally did, he refused rehab with a one-liner that sounded exactly like something Waylon Jennings would say, “Betty Ford didn’t get me on it and she can’t get me off it.” He drove to a cabin in the Arizona desert and went cold turkey for 30 days with nothing but Jessie, his willpower and $20,000 worth of cocaine sitting on his tour bus outside as a test he refused to fail.
When it was over, he told Jessie to go flush every last gram and she did. Willie Nelson cut off his famous red braids and had his wife Connie hand deliver them to Waylon as a sobriety gift and Johnny Cash threw a party. A few years later, when Waylon was in the hospital for heart surgery, Cash came to visit him and during that visit, Cash mentioned some symptoms of his own that turned out to be a life-threatening blockage and they both ended up having bypass surgery in the
same hospital, recovering in rooms on the same hallway because even their bod.i.es were determined to keep them together. Then, without telling a single person, the high school dropout started studying for his GED on his tour bus, watching educational tapes between shows until he passed the exam at 52 years old, all because he wanted his 10-year-old son to know that getting an education actually mattered.
I knew on the other side of that door there was a man who was educated. He did not do a single interview about it and he did not need anyone to know. The same stubbornness that made Nashville hate him was what saved his life and less than a year after getting clean, that stubbornness was about to matter in a way that nobody, including Waylon himself, could have possibly predicted.
Years later, Waylon’s son Shooter would say something about his father that cut through every legend, every headline and every outlaw myth that Nashville had ever built around the man. “The biggest misrepresentation that was always around my dad,” Shooter said, “is that he was this tough guy or the outlaw thing or whatever because he was somebody who really just cared about other people, who cared about music and that was it.
” But caring about people and treating them well are not always the same thing and Waylon Jennings knew that better than anyone. He was married three times before he met Jessie Colter and every one of those marriages ended because Waylon was not the kind of man who could bend for anyone, even the people who loved him.
That two and a half million dollars in debt was actually just the first of three times he went completely broke and at least one of those financial disasters was made worse by a manager named Neil Reshen, a man Waylon had personally recommended to Willie Nelson as a lawyer and a CPA when Reshen was neither of those things.
In fact, I picked all the wrong things about Hank Williams and you all wrote that song on there called the Hank Williams Syndrome. The Hank Williams Syndrome was, you know, write some great songs, have some big hit records, drink a whole lot of whiskey, chase a lot of women and become a legend and d.i.e. And maybe not necessarily in that order.
Reshen’s negligence cost Willie over $2 million in unpaid IRS taxes and Waylon was too consumed by his own addiction to notice what his own people were doing to his closest friend. The grudges he carried were lifelong, absolute and completely unforgivable in his eyes. He felt swindled by Merle Haggard in a poker game early in his career and never forgave him despite decades of sharing the same industry, the same friends and the same stages.
He and Tompel Glazer, the man who helped him build the outlaw movement from scratch, stopped speaking entirely after a cocaine-fueled falling out over money and they never reconciled before either of them d.i.ed. And when George Jones came to his house drunk one night and punched him in the face, Waylon tied Jones to a tree where Jones reportedly sat screaming, “I’m the greatest country singer of all time.
” while Waylon looked at him and said, “Yeah, and you’re tied to a tree.” He admitted publicly that by the end of his drug years, he was killing the people around him without even realizing it and that the damage he did to the people who loved him most was something he could never fully undo. He was not a hero in any traditional sense of the word and he would have been the first person to tell you that.
“I’m just a man,” he once said, “no more or no less. Bad is the worst, good is the best.” But being real about your own failures is its own kind of courage and in January 1985, that courage was about to be tested in a room full of people who had far more to lose than Waylon Jennings ever did. And then I realized I’ve never let anybody run me off from nothing.
A few weeks before the biggest recording session in music history, a charity single from Britain had already shown the world exactly what happens when famous people try to help a country they do not understand. The song was called Do They Know It’s Christmas? and it featured some of the biggest names in British music, Bono, Sting, George Michael and it raised millions of dollars for famine relief in Ethiopia.
But the song’s lyrics asked whether the people of Ethiopia knew it was Christmas time, apparently without anyone involved realizing that Ethiopia is home to one of the oldest Christian communities on the planet, a nation that has been celebrating Christmas for over 1,000 years.
The backlash was swift and brutal with critics calling the song racist, condescending, and patronizing, and the man who organized it, Bob Geldof, would later call it one of the worst songs in musical history. America saw what happened to that song and decided it was going to do better. Harry Belafonte recruited Michael Jackson and Lionel Richie to write a new song, Quincy Jones to produce it, and 46 of the biggest artists in the country to perform it.
And Jackson and Richie spent days making sure that every single line was carefully vetted so that nothing could be misinterpreted the way the British version had been. On the night of January 28, 1985, the artists gathered at A&M Studios in Hollywood after the American Music Awards, and Quincy Jones put up a sign that said, “Check your egos at the door.
” Prince never showed up despite winning three awards that evening. Bob Dylan nearly fell apart at the microphone until Stevie Wonder calmed him down by doing a pitch-perfect impersonation of Dylan’s own voice. And Willie Nelson spent the night talking with Ray Charles about doing something for farmers back home, a conversation that would eventually turn into Farm Aid.
By 3:00 in the morning, everyone was exhausted, and that is when a problem came up that nobody expected. Stevie walks in and says, “I think we need to do I think we need to do something in the language to to why no no we no no we no no.” Michael Jackson had written a nonsense vocal line for the end of the chorus, a made-up phrase that sounded vaguely African but meant absolutely nothing.
And Bob Geldof, the man behind the British version, objected because he thought it sounded like they were mocking the very people they were trying to help. To fix it, Stevie Wonder left the studio, called a friend in Nigeria, and came back with an actual Swahili phrase that he wanted to use instead. The room went completely silent because 45 of the most famous musicians on Earth did not want to be the one to challenge Stevie Wonder.
But Waylon Jennings, the country outlaw who had spent his entire life walking out of rooms when something did not feel right, looked around at the silence and said, “Well, ain’t no good old boy ever sung Swahili. I think I’m out of here.” Waylon walks out of the door. I’m not dealing with this. I don’t know what that means, but I am not going to sit and we lost Waylon, right? He walked out of that studio, and his exit broke the dam wide open.
Ray Charles said, “It’s 3:00 in the goddamn morning. I can’t even sing in English no more.” Cyndi Lauper compared it to singing to the English in German. Geldof himself, the man who had already lived through the cultural disaster of the British version, told Stevie that the song was not meant for the people who needed help.
It was meant for the people who could provide it. And then someone pointed out that Stevie had secretly brought two Ethiopian women to the studio to thank the participants, and those women did not speak a word of Swahili because Ethiopia speaks Amharic, not Swahili. The Swahili line was dropped, replaced with “One World, Our Children”, and the song went on to sell 20 million copies, win four Grammys, and raise over $63 million for humanitarian projects across seven African nations.
If Waylon had stayed quiet, if the Swahili had made it into the final recording, the same critics who destroyed “Do They Know It’s Christmas?” would have had an even bigger target, an American charity song for Ethiopia sung partly in a language that Ethiopians do not even speak, made by artists who should have known better because they had a clear example of what not to do.
Waylon did not plan to save that song, and he certainly did not plan to help save lives across a continent, but that is exactly what happened. Muhammad Ali was his son’s godfather, and Charlie Pride, one of the most important black artists in country music history, was one of his closest friends. This was not a man who had a problem with other cultures.
This was a man who had a problem with dishonesty, and when he smelled it in that room at 3:00 in the morning, he did the only thing he had ever known how to do, which was to get up and leave. Decades of cocaine and a lifetime of cigarettes had already taken Waylon’s heart once when he needed triple bypass surgery at the age of 51, and diabetes took the rest of him piece by piece.
He lost his left foot in 2001, spent his final months in a wheelchair, and when the Country Music Hall of Fame inducted him that same year, he was too sick to attend and said the honor meant absolutely nothing because even at the end, Waylon Jennings was exactly who he had always been.
Living legends are dying breed. Way too many of them live. Tell you the truth, I ain’t been feeling real hot lately, myself. In his final months, he took Jessie’s hand and told her something that she said sounded completely different from every other time he had said it in 32 years of marriage, “You were my home.
” On his last Thanksgiving, two months before the end, she asked if he was ready to accept the Lord, and he grinned and said, “I knew you were going to ask that.” And he did. I don’t know how much he understood until the very last, a relationship with Christ. I don’t After Christmas, he asked her to play the old hymns she grew up with while he listened.
His last words were, “Don’t let the boys stop playing my music.” And on February 13, 2002, at 64 years old, the outlaw who cheated d.e.a.t.h on a frozen night in Iowa finally ran out of time. Hank Williams Jr. returned to the Grand Ole Opry after more than 20 years solely to honor him, saying he knew Waylon wouldn’t care him, telling that he had tears in his wrist, there is a gold bracelet that his father gave him before he d.i.ed with seven words engraved on the inside, “The music is in good hands.”
Shooter has worn it while accepting two Grammys, and he once said that everything his father ever did after that frozen night in Iowa came from the same place, a man who knew his time was borrowed and refused to waste a single second of it on pretending. I have a son named Shooter, and he’s a light of my life.
Buddy Holly told him once, “Don’t ever let people tell you you can’t do something.” He never did. Not once, not for anyone, and not for any reason. And because a man from Littlefield, Texas refused to be anyone other than who he was, the world is a better place for it. Being authentic is not easy, and it is not free, but if Waylon Jennings proved anything with his life, it is that the cost of pretending is always higher.
You know, when you get out here, they’re not going to run me off here. I will be standing when all of this is faded out. If this story meant something to you, consider leaving a like and subscribing because stories like this deserve to be told.
