Illustration by Marco Ventura

So how would you feel? It’s 1958. You’re 21 years old, spinning wax at a two-bit radio station in the middle of West Texas, just happy to be out of the cotton patch and not knowing nothing about nothing but Ernest Tubb, Pepsi-Colas, drive-in movies, and Moon Pies. That’s you, and one day your good friend, who is also your mentor and role model, who also sees a lot more in you than you see in yourself, waltzes into the booth at the radio station, tosses you an electric bass guitar, and tells you to learn how to play it. He’s taking you on a rock and roll tour, starting next month, January of 1959. A week later, your friend flies you to New York City and puts you up in his Greenwich Village apartment. You sleep on the couch, learn the bass, rehearse with the band, and explore Manhattan. The two of you have your picture made in a Grand Central photo booth. Then you climb on the bus, and in a wink, you’re crisscrossing the frozen Midwest in the dead of winter with a bunch of one-hit wonders, playing rock and roll shows in high school auditoriums and basketball gyms.

By the end of January you’ve played twenty shows. Your friend has decided to take you to London as his opening act, which is nice, but that’s a few weeks away, and right now it’s forty below in Duluth and the heat on the bus is out. The tour moves from Duluth to Clear Lake, Iowa, and nobody has any more clean clothes. West Texas boys (on account of their dirty minds) require clean clothing, so your friend charters a plane from Clear Lake to Fargo so you can all find a laundromat before the next night’s show. After the gig in Clear Lake, however, you and the guitar player get wangled out of your seats on the plane.

“You’re not going with me tonight?” your friend asks. “Chicken out?”

You say no, that the Bopper wanted to fly.

“Well, I hope your damned bus freezes up again,” your friend says.

“Well, I hope your ol’ plane crashes,” you say, and, of course, it does.

Your friend is dead, slammed into a frozen wheat field, and you are sitting in a Minnesota truck stop, staring out at the frozen morning, realizing that, just for a minute there, you were sort of about to feel free. Then you feel bad about even thinking that. You’re nothing now in the middle of snowy nowhere, and the promoters don’t want the band to go home. They offer to fly you to your friend’s funeral, first-class. They offer you more money if you’ll stay on the tour. What decides it, though, is that you are a West Texas boy, a bad-weather cowboy, and a man of your word. So, like a fool, you stay, but you get no tickets, first-class or coach. You get no money, and at the end of the tour, in a daze, you go home. You’ve got no friend and you’ve got no future. How do you feel?

Well, first, you’re extremely angry, and second, you don’t care anymore. About some things (like businessmen, lawyers, and bourgeois respectability), you will never care again. You’ve just been awarded a thirty-day doctorate in the music industry, so, from Jump Street, you trust no one except out of laziness and make few friends because, somehow, it seems, you kill your friends, and anyway, you are too far gone for any but the farthest out. From now on you will sit a long way back from the screen and see yourself acting out the roles that life requires of you—son, friend, lover, husband, music star, culture hero—but you will never take any of them very seriously.

You’re plenty screwed up, in other words, and if you had a shrink, if anybody in West Texas had ever heard of a shrink, he would probably diagnose a permanent case of low-grade depression, dissociation, and survivor’s guilt, along with a heavy dose of the old And Suddenly syndrome. He would probably prescribe the pills you’re taking anyway, because at this point, you are morally certain that the better things get, the more likely they are to blow up in your face; that the brighter the sun, the softer the woman, the sweeter the song, the darker the oncoming storm. The future closes like a shutter in these moments, so you live in the music, which has its own time. You can strip it down, tighten it up, clean it off, and ride it like a rising wave. The music, in the moment of its making, sets you free, but it doesn’t cure anything—and, really, it never will.

ON FEBRUARY 13, 2002, in Chandler, Arizona, Waylon Jennings died in his sleep, at the age of 64, of having lived. Six months later, we gathered in Lubbock at the second annual Buddy Holly Music Festival and Symposium, to remember him together. Waylon’s son, Buddy, was there, as were Richie Albright and Billy Ray Reynolds, his primal rhythm section. Billy Joe Shaver, who wrote the archetypal Waylon songs, showed up, and Lenny Kaye, who co-wrote Waylon, the autobiography, flew in from New York, on leave from his gig with Patti Smith. I flew in from Las Vegas to reminisce about my years as an embedded journalist in the outlaw music movement. We all sat at a long table in a white conference room, like a posse without the sheriff.

In ragtag fashion, we projected the man we knew back onto the things we had heard and, in doing so, imagined the narrative that opens this essay. It seems a plausible one to me, and all the more plausible since we had known Waylon Jennings at various times and in varying circumstances, and clearly, we knew the same man. We recognized his preternatural, ironic self-awareness, although we didn’t all call it that. Billy Joe, in fact, looked at me funny when I used the phrase, but we all located the trick of his charm in his benign sense of his public persona as a crazy cartoon of himself. Somehow, he could throw bullshit at you with one hand and wipe it off with the other. In a world full of evil dudes pretending to be good guys, Waylon was a good guy pretending to be an evil dude and never quite succeeding.

You would see him driving around Music Row in some butterscotch, gold-trimmed, East L.A. pimpmobile, dressed up like the “third outlaw” in a spaghetti western, and you would smile, knowing that no one bore less malice in his heart. Onstage, he would step up to the mike, swinging that Telecaster from his hip, and glare out into the lights, projecting an aura of dark, unrepentant machismo with so much good-hearted irony that the aggression bore only the faintest hint of real menace. Out in the audience, you got the buzz of his sexual charisma, but you knew you were one of the gang, that Waylon was sincere in his insincerity. But it was not all a joke. Some things were taken very seriously indeed, and if you crossed the line, you quickly saw the glint, and things got a little, uh, gritty.

You had to violate the code for this to happen, and those who did invariably thought that it was all a joke, that Waylon was totally inside the ongoing party. Eventually, you figured out that, onstage or off, Waylon Jennings loved the party, the performance, and the costumes. He loved the distance they put around him, but part of him was always standing outside, leaning against the proscenium, watching from the wings and keeping things in line. Proper distinctions had to be drawn, because Waylon had rules. He knew the difference between being a man and being an animal, between being crazy and being insane, between being bad and being mean, between being an outlaw musician, a thieving crook, or just a plain old scuzzball, predatory criminal. He never confused these modes of transgression, and although he lived by the Code of the West—as all West Texans must—Waylon never confused cowboys on the stage and cowboys on the range. He insisted, in his music and in his presence, that these distinctions be observed as a hedge against self-delusion.

It’s clear to me now that Waylon’s discomfort derived in large degree from the self-awareness that made him so appealing.

Having said this, of course, I must concede that guarding oneself against self-delusion has never been a high priority among drug addicts of my acquaintance, myself included. Among this delusional legion, however, Waylon Jennings was by far the least deluded. I remember once, not long after I arrived in Nashville, asking Waylon why the locals took speed rather than smack and barbiturates, like us Manhattan sophisticates did. He said, “Hillbillies and hairdressers take speed because they’re not comfortable, but they still have to work.” That, I thought, just about said it, although it’s clear to me now that Waylon’s discomfort derived in large degree from the self-awareness that made him so appealing.

One night on the highway, in his new shiny bus, on the teetering brink of his pop success, I asked him how he liked his new audiences. “Well, it ain’t exactly living in the love of the common people,” he said dryly. He went on to explain that when you start performing, you play for people who are just like you, and that’s not really performing. Then you perform for people who just like you, and that’s really fun. Then, “if you’re lucky,” you end up performing for people who want to be you, and that’s really not as much fun because these people who want to be you always hate you a little because they’re not you. They secretly want you to fail so you can know how it feels to be them. “Actually,” he said, “it’s not that complicated. There’s a lot of people in a room. One guy’s got the microphone. Everybody else’s got the beer. They’re all having about the same amount of fun.”

I sat there and thought that knowing this much about yourself and your audience was probably not much of a benison for a performer. It does, however, account for some of Waylon’s special virtues. In “Good Hearted Woman,” for instance, there is a line that goes “She loves him in spite of his wicked ways she don’t understand.” Waylon never sang it that way onstage. He always sang “She loves him in spite of his Mickey Mouse ways that she don’t understand.” Because, I think, Waylon knew what wickedness was. He knew he wasn’t it, and his comic vision of Mickey Mouse machismo let everyone in on the joke. He could characterize himself—in a phrase at once self-deprecating and deftly cosmopolitan—as “too dumb for New York City, too ugly for L.A.,” and no other singer in Nashville would even dare.

He could stand in the wings, watching himself onstage, and write, “I’ve seen the world with a five-piece band looking at the backside of me.” I can’t imagine another country performer confident enough in his own masculinity to acknowledge that he knows the band is looking at his butt. And what other leather-clad, asphalt cowboy could walk up to a fellow who’s bitching about somebody being “a goddam queer,” drape his arm around the fellow’s shoulder, snuggle up close to him, and say, sotto voce, “Aw, come on, Hoss. We all just grab onto something warm and worry ’bout the details later.” If you were familiar with the pathological caginess of most Nashville singers, this cowboy hipster candor was scary at first. Then you realized how profoundly Waylon did not care, and ultimately, I think, the magic cloak of this not caring kept him alive for more than six decades. Because the truth was that if Waylon wasn’t on the stage, in the studio, on the bus, or having dinner with his wife, Jessi, he was in trouble or about to be.

His gift to us, of course, had nothing to do with being in trouble, although it got him into some. He made strong music. He sang great songs that said things beautifully and spoke with some precision to the times for which they provided the soundtrack. More than that, of all the artists with whom he is associated, Waylon Jennings had the most passionate sense of how you put things together and what things you leave on the bus. He was an artist, in other words, and an artist of his time. At the exact moment that American painters and sculptors were cutting away the obfuscation and expressive nonsense that had accrued around American art during the post-war period, at the very instant that the kids at CBGB’s were beginning to jettison the pretentious theater that was drowning rock and roll, Waylon was taking country music back where it never had been.

He stripped away the decorative bric-a-brac that had plagued Nashville product for decades and created contemporary roots music in the minimalist tradition—a music that was not really simpler, just stronger, better organized, and more totally focused than anything that came before it. Dispensing with virtually everything but the rhythm track and the vocal, he changed the focus of the sound from the orchestral grandeur of the setting to the sinuous muscularity of the music’s forward drive. Abandoning the pop-hillbilly flummery of contemporary country songs, he embraced the poetic license and compression of lyrics like Billy Joe Shaver’s. In the end, he made a new music that, like the singer of Billy Joe’s song, “left a long string of friends, some sheets in the wind, and some satisfied women behind.”

The trick was in the bass and drums, and Waylon’s producer, Jack Clement, helped with this. As Richie’s drums got sharper and cleaner and the bass got louder, the tempo could get slower and the vocals softer, so everything fell into balance. The songs rode on the bong-bong of this “Cajun march” that Richie and Waylon invented—it sounded like an old four-four but bounced like a bluesy twelve-eight, with hidden triplets flowing through the drum track, accentuated by Waylon’s Telecaster. To Nashville ears, it sounded like nothing or, even worse, like rock and roll, but it moved like a new wheel on an empty highway and still does, although there are no more empty highways and no more hipster cowboys at the Dairy Queen. Even so, history keeps a special place for artists like Waylon who scrape off the paint and carry out the trash, who bet their whole heart on the unadorned shape of the music. You have to be crazy to do it, of course. You know that soon enough the vehicle will be repainted, that stripes, chrome, and all manner of gewgaws will ultimately accrue, but what you have done doesn’t go away. It survives at the heart of the music.

AND WAYLON SURVIVES AS WELL, on his records, of course, but most profoundly in the memory of fading gypsies like those who gathered in Lubbock, who never saw bad done so well. This is the picture of Waylon that I carry with me today: We are milling around the crowded greenroom after a show in Atlanta. Waylon is flopped down in the middle of a leather couch, flanked by two exquisitely coiffed, extremely plump white ladies. The ladies are attired in pastel pantsuits, and the three of them make a nice tableau—the gaunt King of Darkness bracketed by two painted and powdered Easter eggs. Waylon sits forward with his elbows on his knees, grinning and soaked with sweat. His hair hangs in wet, greasy ropes, some of it plastered across his forehead. His shirt is stuck to his body, and his wristband is stained with dark blotches. He sinks heavily into the pillows of the couch while the fat ladies seem to float weightlessly. I am imagining the strain the ladies are putting on their knees, trying not to look heavy, when I realize that, at that moment, they are not heavy at all. They are in heaven.

I sit down on the arm of the couch and find the three of them in a deep discussion about the almost insurmountable difficulty of running a beauty salon in Atlanta, Georgia, what with taxes, zoning, sorry help, and the burgeoning complexities of interracial hairstyling. Waylon is contributing what he can, which is more than I would have expected. His limited experience of beauty salons, I surmise, has been considerably enhanced by his wide experience with beauticians. Also, Waylon is a small businessman himself. As he points out, he started off as a very small businessman, picking Texas cotton and getting paid by the pound. The ladies chatter away, giddy but perfectly at ease. They are telling this dangerous outlaw things they have never told anyone, but they are not complaining, as they are wont to do, because Waylon is not a complainer and he is contagious.

Whatever they expected as they tiptoed backstage, it was never this! They are having a conversation with Waylon Jennings! It’s better than the sex they fantasized about and thought they wanted but didn’t really. Waylon knows this. He knows that, as a culture, beauty-salon ladies are incurably romantic and less worldly than they like to pretend. They are not prudes, exactly. They will have sex with you if they must, but what they want is Scarlett and Ashley. They want the rituals of courtly flirtation, and Waylon, with his devil smile and attentive gaze, is giving them that. It occurs to me, as I blatantly eavesdrop, that Waylon is selling a hell of a lot of records with this little gesture. Then I feel bad for having thought it, because Waylon Jennings, in that moment, is clearly happy as hell to be chatting with the fat ladies, behaving like the perfect young cowboy, being thoughtful and curious and whimsically generous, living in the love of the common people.