One of the Nashville artists who would later form the Outlaw country movement, Waylon Jennings had been kicking for years, but was lucky to be alive. In 1958, fellow Texan Buddy Holly had produced Jennings’s “Jole Blon” and “When Sin Stops (Love Begins)” and then picked him to play bass for his Winter Dance Party Tour. Holly arranged for a tour plane, but Jennings gave away his seat the night the plane went down and claimed the lives of Holly, the Big Bopper, and Richie Valens. “The day the music died,” Don McLean called it in his elegy “American Pie.”

Jennings moved to Arizona and formed the rockabilly Waylors. He got signed by Herb Alpert’s A&M Records but was ignored because he wasn’t folk, the hot trend of the moment. Things started rolling once Chet Atkins signed him to RCA and he moved to Nashville; his first recording session in Music City was on March 16.

June Carter had brought Johnny Cash to see Jennings play in Arizona. Both men had worked in the cotton fields, and knew all the same obscure music by country guys from the 1920s. Cash wanted a place to crash when he was in Nashville, so he and Jennings got a one-bedroom with two king-size beds. They’d always forget their keys, lock themselves out, and have to kick the door in. Jennings hid his pills behind the air conditioner; Cash hid his behind the TV.9

In his autobiography, Jennings wrote of Cash:

We were so much alike in many ways, it was scary. We both dressed in black . . . It’s a worn-out word, but we were soul mates . . . We flipped over each other from the moment we met, though at first we stood back. It was so sudden we were kind of afraid of each other. John and I were both manly men, and we liked to walk macho and talk macho; but after a while we learned we could be ourselves . . . We’d just get giddy and silly around each other, and laugh a lot. That would be when I’d be calling him John. Or Maynard. He had a lot of names. “Johnny Cash” was formal, as in “Mr. Cash.” There was Johnny when he was just lounging around. And then there was Cash. Sometimes you couldn’t tease John or he would become Cash. He was very seldom Cash with me. Cash was usually when he was mean, or when he was on drugs.10

Jennings’s first country hit, “That’s the Chance I’ll Have to Take” opens with a lonesome harmonica that echoes like the wide-open spaces of Arizona and Texas. A little folk seems to have rubbed off on it. In fact, his first Nashville album was called Folk-Country, recorded from March to July. Like Cash, Jennings dug Dylan and had covered “Don’t Think Twice, It’s Alright” live; later he’d tackle Dylan’s “I Don’t Believe You” and the Beatles’ “Norwegian Wood.” Another of his singles, “Anita, You’re Dreaming,” was based on the same traditional Mexican folk melody Dylan had used for “To Ramona.”

After Jennings’s rocking “Stop the World (and Let Me Off)” made it to No. 16 (country), a film tailored around Jennings, called Nashville Rebel, went into production and was released the following year.

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