One morning in 1977, Alex Chilton, 26, former lead singer of the Box Tops and of Big Star, very likely hungover or still drunk, appeared before an American studies class at the University of Texas to discuss his career in music and his thoughts on the present state of rock and roll. "Rock and roll is supposed to be out of control," Chilton told the boys and girls, "and it's crazy and it's supposed to drive you crazy." To illustrate his point, he serenaded the undergraduates that morning with a little ditty called "Riding Through the Reich," the lyrics of which were inspired by the scribblings of a white-supremacist spree killer, he said, and accompanied the tune of "Jingle Bells."

This was Alex Chilton's MO. He was not a Nazi, but he did embody the juvenile irreverence of rock-and-roll "crazy" while tending to drive plenty of others crazy at the same time, including his bands, his producers, his girlfriends, and his own fans. The title of Holly George-Warren's new biography of Chilton, A Man Called Destruction: The Life and Music of Alex Chilton: From Box Tops to Big Star to Backdoor Man (Viking), couldn't be more on the mark: Alex Chilton was a destroyer, a gleeful insurgent of American rock whose career moved erratically in zigzags and curlicues ("I just do these things," he said of his many disparate projects). He's also responsible for some of the most beloved ear candy since the Beatles, as verified by the many impassioned tributes upon his death in 2010 (including one from the floor of the U.S. House of Representatives). And that's not to mention the scores of musicians who knelt at his throne while he was alive, from the Bangles to Elliott Smith. Still, Chilton lived out a career spent sometimes in poverty, without ever graduating from the dubious honor of Cult Hero. What kept him the one-eyed king of that land of the blind, the American rock underground? The answer, George-Warren has shown, is that he lived-or at least didn't die.

The bizarre trajectory of Chilton's career begins at age 16, when he records vocals for a track called "The Letter" with his garage band the Box Tops. "The Letter" becomes a massive hit, and Chilton goes from farting around the Memphis suburbs to national television, playing 15,000-seat arenas, opening for the Beach Boys, and right to the bank with a fat check made out to America's Youngest Hitmaker. And there are girls, one of whom will make him a father before he can legally drink in Tennessee (the first thing fast proving no more a burden on his conscience than the second). It's a rock-and-roll pipe dream come true, but the constant touring and industry hoop-jumping wears on the kid: "It was sort of a job to me," he's quoted as saying later. "I wasn't such a great fan of our group that I was really caught up in thinking that I was a tremendous great artist or anything." By the time the Box Tops fold in 1969, Chilton, eager to grow as a songwriter but already yesterday's news, finds himself in the peculiar position of having started his career from the absolute top-a number-one record. And where can you go from there?

The answer, it turns out, is #1 Record, the first album by Big Star. The brainchild of striver-loner Chris Bell, Big Star (so named with fingers crossed) becomes Chilton's big-boy band, a fresh start and a fresh sound inspired by Bell's and Chilton's shared love of the British Invasion. Their combination of unpretentious ballads, like Chilton's fingerpicked "Thirteen," with windows-down, Friday-night jams like "In the Street" (which Cheap Trick would later cover as the theme song to That '70s Show) carries over to the follow-up, Radio City. What does not continue is Chilton's partnership with Chris Bell, who quits his own band a heartbreaking mess-furious that #1 Record hasn't sold well despite the enthusiasm of critics, frustrated with the attention (when there is any) given to Chilton, and by most accounts deeply troubled by his sexuality. He also attempts suicide, as Chilton does in 1967 and does again in 1976.

Success continues to evade Big Star under Chilton's leadership, though Radio City-featuring the stillborn Christ-child of a hit, "September Gurls"-and the third album, Third, are now considered masterpieces. The chaotic recording of Third, Chilton's baby, is the beginning of a supernova burnout (the album's producer characterizes Chilton's approach as, "This is gonna be mine, so I'm gonna be the one who fucks it up"-less a threat than a promise). In 1975, Big Star burns out in the cold, dark galaxy of pre-punk, with Chilton's addictions and his ego serving as no small reasons why. He is only 24.

From here, Chilton's story has always been seen as one of great potential frittered away. George-Warren doesn't entirely discredit that view, but she also rehabilitates his long twilight and suggests in the process an alternative constellation of his achievements that extends beyond Big Star. She draws attention to his 1979 solo album, Like Flies on Sherbert, for example-a brilliantly deranged deconstruction of '50s rock that showcased his embrace of punk not only as a return to roots but as an ennobling of the amateurism and bullshit artistry he found so thrilling. George-Warren quotes a producer from the time: "His whole concept was, If I were a thirteen-year-old right now, and I were just learning my instrument, how would I play guitar?"

Chilton contents himself by moving out of the spotlight too, producing the first Cramps singles and gigging as a sideman with avant-rockabilly goons Tav Falco's Panther Burns. In the early '80s he moves to New Orleans-ironically, to clean up-where he would live until he died. He works as a dishwasher, a janitor at a music club, and a tree-trimmer, subscribing at different times in his post-Big Star life to astrology, communism, and Wilhelm Reich's orgone theory. By the mid-'80s a new generation of guitar bands is hailing his influence in interviews, and a single by the Replacements introduces swarms of flannel-clad Gen-X youth to a hero they didn't even know they had. "Children by the millions sing for Alex Chilton when he comes 'round," Paul Westerberg daydreamed. "They sing, I'm in love/ what's that song?/ I'm in love/ with that song."

Children never do come by the millions, of course, but Chilton continues to work steadily and quietly, honest about his own limitations ("I'm writing really vacuous pop songs these days," he told George-Warren in the '90s) and never quite buying into what the kids were saying about Big Star. He finds fertile soil in the ashes of every torched expectation, making music as if he had no other option, which he doesn't, no matter how half-assed or half-hearted the result. "I figure if I can get myself together at some point," he says at a particularly low point, "I might have a real shot at making a lot of bread-making music. But it doesn't matter. I just want to enjoy it."

As the book progresses, the steady accumulation of self-indicting or otherwise-negative anecdotes about Chilton's behavior tips the scales of our sympathy against him, which shouldn't be too surprising when you consider that, having forfeited the life of a normal teenager to the Box Tops, his maturity apparently stunted somewhere around age 17. There's Alex onstage trying to sing through a mouthful of fried mushrooms; there's Alex in the studio "shoot[ing] Demerol down his throat with a syringe"; there's Alex starting shit at a Jerry Lee Lewis gig in Memphis; there's Alex playing "Chopsticks" at CBGB's; there's Alex getting a blowjob onstage. You can hear the laughter of exactly one person through it all.

But the laughter is tragic. Like Kurt Cobain did 20 years ago, and like Chilton's old partner Chris Bell did in a car around a tree in 1978, Alex Chilton might easily have died before he turned 30. That he survived himself may be a testament to how at peace he really was with being a hero. Self-doubt and self-sabotage aside, all he wanted was to enjoy it.