This article originally appeared in the January 1988 issue of SPIN. Waylon Jennings was born on June 15, 1937. In on honor of what would have been his 83rd birthday, we are republishing the interview here. “You’re gonna get in trouble if I write this.” “I don’t care. You write what I tell ya.” Waylon Jennings, looking more like an outlaw biker than a cowboy, is dressed in black except for his nylon racing jacket. His trademark black hat never leaves his head. He turned 50 this year and he looks it. He also looks healthy, if weathered. There is no sign of his 20-plus-year addiction to pills and cocaine. He chain-smokes. He’s slightly nervous, but becomes more relaxed as the interview progresses Waylon is in New York, a city he first visited as one of Buddy Holly’s Crickets, to promote ...