For neither the first nor last time, ol’ Waylon was ticked. The year was 1987, the scene was the set of a Steve Earle video, and Earle sensed something was amiss as soon as Jennings, who was filming a cameo, came into his trailer grumbling. ”He’d just made a movie and hated it,” recalls Earle, ”and to him this was more of the same. I said, ‘If you don’t want to do something, just tell the director.’ And Waylon said, ‘Well, I just told him to kiss my legendary ass.”’

The story is classic Jennings. The irascible, bedraggled king of renegade country arrived quietly, in 1937 — his small-town newspaper didn’t even publish news of his birth, he claimed — and departed quietly, dying in his sleep at his home in Chandler, Ariz., on Feb. 13 of complications related to a series of health problems, including diabetes and heart ailments. But in the 64 years in between, Jennings left a huge, ornery footprint on the music, expanding both its artistic possibilities and its audience.

He led several lives: disc jockey in Lubbock, Tex., in the mid-’50s, then bassist for Buddy Holly. The latter gig didn’t last long: Jennings gave up his seat to the Big Bopper on the ill-fated 1959 flight that took his life and those of Holly and Ritchie Valens. Jennings’ joking last words to Holly (”I hope your ol’ plane crashes”) haunted him for years. In the mid-’60s came life No. 3, as a smooth-faced Nashville balladeer. But by the middle of the following decade, Jennings had taken the reins of his music — stripping it down and sexing it up, marrying his weary, predatory baritone to the speed-bump thump of his guitar. His hair and beard grew out, his hat turned black, and a new, iconic Jennings — a carnal country Mephisto — was born.

So was a new sound and sensibility, dubbed the Outlaw movement. With such like-minded rebels as Willie Nelson and Kris Kristofferson, Jennings led a Nashville coup d’etat, steering the music away from Hee Haw and orchestrated mush. Three decades later, with Music City once again sanitized and Nelson as much a piece of Americana as the Washington Monument, it’s almost impossible to still picture these revolutionaries — rumpled, hippiefied good ol’ boys dripping with rock-star allure — rolling into town. ”Waylon made it possible for me to do what I did,” says second-generation dissident Earle. ”When you start looking for a role model for how to carry yourself around the music industry, you look to Waylon and Neil Young and Tom Waits. And you don’t need to look any further.”

Jennings was fond of the old ways, too — the hard life of one-nighters, cocaine, alcohol. By the early ’80s, the combination had derailed his life and career (although his longtime marriage to singer Jessi Colter stayed on track). The music was never quite the same, but on a positive note, neither was he: Starting in 1984, he began a long journey to sobriety. Most importantly, his spunky spirit — tightly wound but bighearted — never left. Last year, Jennings, confined to a wheelchair and on the verge of having his left foot amputated as a result of various illnesses, visited Nashville’s Country Music Hall of Fame. ”It’s a great place,” he told museum director Kyle Young afterward. Then, a few months later, Jennings blew off his own induction ceremony. ”I wasn’t surprised,” says Young. ”It was part of the persona.”