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