In September 1967, a group of young men in matching manila-envelope-colored suits played their latest single on a regional Atlanta TV show called The Village Square. The Memphis boys in the Box Tops topped the charts for a month that autumn with “The Letter,” a compact, bluesy pop song driven by the bulldog growl of their 16-year-old lead singer Alex Chilton. In those days, earnest lip-syncing was the de facto mode for such TV performances, but Chilton smoked a joint before the taping and couldn’t be bothered to even pretend. For half of the song, he mouthed some words resembling the lyrics, then gave up and stood there, zoning out, eventually giggling at the ridiculousness of it all. When the knockoff Dick Clark host came over to ask him a canned question (“Is there really a letter?”) Chilton botched the timing of a bit he was supposed to execute that involved pulling a comically long prop scroll out of his pocket. “The song’s only got one verse, er …” he muttered, barely realizing the host had already moved on to the other members of the band.

One year earlier, when Chilton auditioned for a local band called the Devilles, he had to call their 19-year-old drummer and ask whether he could drive him there: “I’m only 15, so I don’t have my license yet.” But when he ripped into “Mustang Sally” at the audition, the guys were in awe. The kid sounded almost laughably old, like a grown, grizzled man three times his age. “Alex was one of the few people I’ve ever seen that at an early age had his own voice,” his first producer, Dan Penn, later recalled. “He had something in him when he came into the studio.” The Devilles played enough local shows to learn there was another band called the Devilles and, after they changed their name to the Box Tops, Penn invited them to a nearby studio to cut a song he’d written. The night before he recorded his vocal take on “The Letter”—which would improbably go on to become, in his biographer Holly George-Warren’s telling, “the biggest hit single ever recorded in Memphis, Tennessee”—Chilton did not grant his voice any beauty sleep. Instead he stayed up until dawn, drinking, smoking, and fooling around with his girlfriend in a cemetery. “I was a little hungover,” Chilton later recalled of his bleary-eyed first appearance in a professional recording studio, “been out in the dewy grass in my bare feet all night, and certainly wasn’t in the best shape I could have been in.”

Getting it right on the first try is funny that way. The rawness of Chilton’s vocal gave the Box Tops’ debut single some grit, and before long it was a nationwide smash. (The young band’s brief, meteoric post-Beatles rise calls to mind the plot of That Thing You Do!) And so, stemming from the very first time he ever stepped foot in a recording studio, Alex Chilton quickly became hang-out-with-the-Beach-Boys famous. Drop-out-of-high-school-to-tour-the-country famous. Smoke-Wilson-Pickett’s-band’s-weed famous. Father-at-least-two-children-before-turning-18 famous. Penn and everyone else making money off the band tried to bottle Chilton’s lightning, succeeding just one more time with “Cry Like a Baby,” which hit no. 2 on the Billboard charts. (It featured backup vocals from the Sweet Inspirations, a gospel group helmed by Whitney’s mother Cissy Houston.) Time kept accelerating for the kid with the old-man voice, and as the Box Tops’ pop magic wore off he learned something important that he wouldn’t be able to articulate until years later. “Here I am at the top,” he said, “doing something I don’t understand and don’t really have any feeling for and getting really famous for it. Gee! But it’s good to find that out when you’re young: Fame can make you money, but it’s a big pain in the ass. There are real advantages to being unknown.”

There are downsides, too. By the early ’80s, a 30-something Chilton was broke and broke-down in New Orleans, making a living trimming trees, mopping floors, and washing dishes. For long stretches he didn’t even own a guitar. That unknown period came a decade after his run in Big Star, a band that saw little success during its lifespan but later inspired a devoted cult fan base. By the ’90s, a generation of alternative rockers had canonized Chilton as a patron saint of indie rock, a key figure responsible for inventing what came to be known as power-pop. R.E.M. worshipped them; guitarist Peter Buck has mentioned them in the same breath as the Beatles, Dylan, and the Rolling Stones, once telling an interviewer, “We’ve sort of flirted with greatness, but we’ve yet to make a record as good as Revolver or Highway 61 Revisited or Exile on Main Street or Big Star’s Third.” Jeff Tweedy is also a huge fan, and it’s easy to see a connection between Third’s deconstructed melodies and those of Wilco’s Yankee Hotel Foxtrot. “I never travel far without a little Big Star,” Replacements lead singer Paul Westerberg declared on the 1987 song “Alex Chilton.” When Counting Crows played “Mr. Jones” on Saturday Night Live in 1994, Adam Duritz changed the Bob Dylan lyric to “I wanna be Alex Chilton”—a po-faced homage that I find somehow embarrassing for all involved. With all he’d lived through at that point—the fleeting highs and the years-long slumps, the creative frustrations and the commercial disappointments—did a dude playing his hit single to a national television audience really want to be Alex Chilton?

At the very least, it sometimes seemed like Alex Chilton didn’t even want to be Alex Chilton. Two years prior to that Counting Crows performance, in 1992, Chilton told an interviewer, “I’m constantly surprised that people fall for Big Star the way they do … People say Big Star made some of the best rock ’n’ roll albums ever. And I say they’re wrong.” A frustrating aspect of being a Chilton fan is that, until his death from a heart attack in 2010, he and his admirers were often at odds about what they considered his best work. Now, the release of two new compilations from his often overlooked later years—a collection of his ’80s work called From Memphis to New Orleans and an album of jazz standards named for his childhood address 987 Robin Hood Lane—once again sheds light on that tension. Casual listeners will have trouble reconciling their sparse arrangements with Big Star’s signature lush sonics, while Chilton completists will find themselves lingering on one of the less glamorous eras of his biography. And yet, as Rob Hoerburger put it in a New York Times Magazine obituary, “If one measure of rock stardom is being your own man, then Chilton, whose career was tracked with impurities, might have been the purest rock star of all.”

I am among a generation of people who first came to Chilton’s music through a wide variety of covers of his tender 1972 song “Thirteen”—first by the alternative-rock band Garbage and then a little later an aching, faithful homage by Elliott Smith that would appear on his posthumous compilation New Moon. (Introducing a version of the cover accompanied by Jon Brion, Smith called Big Star “one of our favorite bands.”) The song has been covered by so many artists that the music website Stereogum has compiled an entire blog post titled “Gotcha Covered: ‘Thirteen.’” I doubt I am alone in thinking it is one of the most stirring encapsulations of the superpowers granted by young love and burgeoning musical fandom: “Won’t you tell your dad get off my back? Tell him what we said ’bout ‘Paint It Black.’”

Ever self-abnegating, Chilton said of a composition that has become something akin to a modern-day standard: “That’s one of my almost-good songs.”

In Holly George-Warren’s excellent Chilton biography A Man Called Destruction, a childhood friend recalls first meeting him in middle school, at a ballroom dance class he voluntarily attended—“a sure way to meet girls.” One day he showed up “with his pockets full of firecrackers,” which is somehow not a euphemism. “We were all awkwardly standing around waiting to be asked to dance,” remembers the female friend. “A loud noise came from over by the door to the back of the gym. It turned out to be Alex, of course. Not just one firecracker, but a string of them.”

The idyllic early years of Chilton’s life took place in that suburban house at 987 Robin Hood Lane. Sounds, myths seeped into his pores down there: Elvis played his older siblings’ high school auditorium, and, Chilton later recalled, “He happened to live not too far away and you often saw him driving down the street in a Cadillac.” Alex was the baby of the family, left to absorb the jazz music of his musician father and the rock ’n’ roll favored by his older brother Reid. But a tragedy caused him to grow up fast. In 1957, 17-year-old Reid drowned in the bathtub after having a seizure. Six-year-old Alex was with his mother when she discovered the body.

Then things got a little firecracker-wild. The family moved to a different part of town and took up a bohemian lifestyle. Alex’s mother opened a small art gallery on the first floor of their home, and local eccentrics got in the habit of stopping by, including the soon-to-be-famous photographer William Eggleston. In the Big Star documentary Nothing Can Hurt Me, producer Jim Dickinson (who’d later go on to work with Chilton, doing brilliant production work on Third) remembered that the first time he met Alex he was 11 or 12, running around on peyote that Eggleston had offered him. Dickinson remembered chuckling to himself, “This kid’s gonna have a unique life.”

As surreal as the Box Tops’ success was, it was also just the sort of thing that happened to a kid like Chilton. As he later realized, though, it screwed with his biological clock in ways that would affect the music he’d make. “I had to quit school at 16 to be in the Box Tops,” he once told a journalist. “So here I was, traveling across the country, surrounded by all these businessmen and older influences. I had left my own peer group completely, and in a way I never really advanced past that. [In Big Star] I was 21 … but I was writing like I was 16 or 17. So what I was writing about on that first Big Star album was just going back and trying to catch myself up.”

Chris Bell was an intense, timid kid from a family that had made a fortune running a Memphis fast-food chain called Danver’s. When he was stoned and even when he wasn’t, he heard beautiful music in his head. During his sophomore year in college he started attending an informal recording and engineering class at John Fry’s local recording studio Ardent, hoping to acquire the tools to get those sounds out of his skull and into the open air. A world-weary 20-year-old Chilton was back in town then, and Bell thought the guitarist and singer would complement the sound of the band he was assembling. “Basically what I did was join Chris’s band,” Chilton later said of Big Star, the group of which Chilton would eventually become frontman.

Most young bands find their sound by flailing around in the garage. Big Star had a state-of-the-art studio as their playground (drummer Jody Stephens has referred to Ardent as “Disneyworld”), and that’s a large part of why their records continue to sound so innovative and pristine. They’re the rare band adored by both pop lovers and audiophiles alike because they were students of the songbook as much as the studio. Chilton, Bell, Stephens, and bassist Andy Hummel had more or less free reign to hang out at Ardent, sometimes even stumbling in drunk in the middle of the night to try out the kind of experimentation that would make sense in an altered state. The brilliance of #1 Record, Radio City, and Third is the price paid for occasionally having to break up fist fights or clean booze out of the innards of a mixing console. (Big Star hold the dubious distinction of getting into more trouble at a TGI Fridays than perhaps any other band in rock history.)

If you came to it late—and 99 percent of listeners do, because of a botched distribution deal that meant it sold squat—Big Star’s debut album #1 Record is the sort of album that makes you feel grievously lied to by classic radio. “While you were playing ‘Whole Lotta Love’ every hour on the hour,” you want to scream at the radio programmers of your youth, “Was there seriously no room for ‘The Ballad of El Goodo’?” The cheekily titled record is fully realized, blossoming with the confidence of an established group. The follow-up, Radio City, has a coexisting lacquer and a grit—it glitters like steel wool. A lifelong devotee of astrology who was known to ask people their birthdays before getting involved with them (musically or romantically), Radio City was recorded during a time Chilton found himself juggling relationships with two women, both of them Libras. Hence “September Gurls,” a melancholy pop ditty that would become one of his most beloved songs. (“December boy’s got it bad,” sang Chilton, an incurable Capricorn.) Again, it was the results of working within limits and idly experimenting. Of the head-spinning layered guitars on Radio City’s “Daisy Glaze,” Chilton once winked, “Those overdubs were just kind of kinky things we did on evenings.”

Most days I’ll tell you that’s my favorite Big Star song, “Daisy Glaze.” Some of those days, if I’m feeling particularly audacious, I’ll tell you that Jody Stephens’s three thump-thump-thump bass-drum kicks that hit at the 1:51 mark in the song and rev up a sudden tempo change is my favorite moment in all of popular music. Since it’s one of those days, I will say that it’s all there, everything, compressed into that tiny space, like the big bang in reverse: The whole endless cosmos of Big Star. The ups and the downs, the uppers and the downers, the shrugging ascent of Chilton and the sad demise of Bell. In his book about Radio City, Chilton told the writer Bruce Eaton that the tempo change in “Daisy Glaze” was inspired by Movement One of Handel’s Concerto Grosso Number 7 Opus 6. There, too, is all the sacred profanity of rock ‘n’ roll compressed into a tiny contradictory speck: The idea that you can reference George Frideric Handel in a song about scoring drugs and trying/failing to get laid. “Now I’m in a bar,” Chilton sings, stupidly and brilliantly direct, kicking off the song’s rollicking second section. At the core of Big Star’s sound is the assertion that despair and joy, creation and destruction, are never far from one another. Amid a swirl of baroque homages and Lou Reed quotes, here are the lyrics Chilton sings at the end of this beautiful song:

And I’m thinking, Christ

Nullify my life

Nullify my life

You’re gonna die

Yes, you’re gonna die

Like a flower

You’re gonna die

You’re gonna decease!

Bell was no longer in the band by the time this song was written. Chilton/Bell is sometimes considered the Lennon/McCartney of Memphis, but that was never quite right: When Paul left the Beatles, after all, the band broke up. And anyway, both of them lived to see 40. Bell made it to 27, embittered that his band kept going without him. He put out one proper solo single in his lifetime, “I Am the Cosmos,” released just before he died when he crashed his car into a utility pole. His funeral was on Chilton’s 28th birthday.

Who doesn’t know some version of those guys: The one to whom everything comes so easily he’s bored by it, and the restless striver who’d kill for that kind of luck? As friends, they can drive each other out of their skin. But put them in a band together and the music they make might break your heart.

Chilton and Bell recorded together one last time, when Chilton sang backup on the gentle acoustic “Cosmos” B-side “You and Your Sister.” In Nothing Can Hurt Me, Memphis musician and writer Rick Clark sums up the song’s wrenching power. “Chris’s voice, he’s pushing against his limitations and sometimes he sounds like he is one breath away from evaporating in front of my ears,” Clark said. “Alex’s genius happened because he could so carelessly throw things away. And I can tell that Alex is probably just tossing his lines off. But there’s something about the way that the two of them sing together on that take. Half of the time I listen to it, I’m reduced to tears.”

At times throughout his career, it could seem like Chilton was making a game of how little he was trying. Once in the late ’70s, while producing music for the rockabilly punk band the Cramps, Chilton mixed most of the tracks with his socked feet instead of his hands, just because he felt like it. And yet, opined Ork Records cofounder Charles Ball, who was with him during those sessions: “Just to watch him use his toes there was amazing. He was masterful in the studio.” The kid from the Box Tops still couldn’t lose.

By the mid-’70s, it was almost as though Chilton were courting failure on purpose, to see whether he was actually charmed enough to be impermeable to it. The final Big Star album is—artistically speaking, at least—ample evidence that he was. Third is a dispatch from the brink. It’s sometimes called Sister Lovers or Third/Sister Lovers, and this indeterminate state is part of its mythos; it’s a nebula, a shrug, an eternal work-in-progress. I have heard the order of its track list sequenced in at least four different ways, depending on the version. It takes the band’s marriage of exuberance and despair to an extreme: Some of the most uncomplicatedly beautiful and upbeat songs Chilton ever wrote (“Jesus Christ,” “Stroke It Noel,” “Thank You Friends”) sit alongside deconstructed compositions like “Kanga Roo,” drugged reveries like “Downs,” and astonishingly morose tracks like “Holocaust.” It is an album in a sustained state of collapse. That it is as gorgeous and moving as it is feels a fortunate accident, or even a provocation.

Chilton moved to New York for a little while after making Third, and he found he was a natural fit in the city’s burgeoning punk scene. In the late ’70s, bands like the Cramps and the Sex Pistols would revive his flagging enthusiasm, though unlike most people, he didn’t see punk as a rupture with the rock of his youth so much as its natural progression. “Good rock ’n’ roll started from the rockabilly singers of the fifties,” he once said. “It has always been wild and out of control, and you had a real chaotic sense, and the punk thing has brought that back pretty strongly. To me, it’s just good rock ’n’ roll.”

In A Man Called Destruction, George-Warren describes Chilton experimenting with some solo material he recorded just before he joined Big Star: He sang one version of the original composition “Free Again” “in his raspy Box Tops voice and another in his midrange.” That’s a crucial way of understanding Chilton, referring to “his Box Tops voice” as though it were a mask he could take on and off at will. Maybe the people who were disappointed by Chilton’s post-Big Star work had been tricked into thinking that “his Big Star voice” was something more natural than just another mask. (When he spoke, Chilton came off like a duke of the Delta, a distinctive drawl that somehow betrayed both his Southern roots and his early Beatles fandom.) For what it’s worth, Chilton had a great punk voice too: He could sound snottily aloof and melodic at the same time, and even when he was falling out of tune there was something compelling about the way his voice broke. “Alex had a way of undercutting himself,” the writer Parke Puterbaugh, who caught many of Chilton’s New York punk shows, once said, “like not wanting things to be too perfect and so deliberately messing them up. [At one gig], he veered badly off course and lost his way on a song or didn’t know it that well and hit some horrible chord—and Alex looked delighted. It just made him happy.”

Maybe I’ve got the same screw loose: The music he made in this era makes me happy too. In 1979, his first proper solo album, the intoxicatingly bizarre lo-fi classic Like Flies on Sherbert (its working title contained a less-marketable sh-word) was released. Sherbert has the foundation of knowing the rules, and the unadulterated glee of shaking them off. (I’m also partial to Chilton’s punk-era collection Take Me Home and Make Me Like It, which features not one but two borderline obscene lo-fi versions of “Jesus Christ.”) He’d denounce so much of his most beloved work, but even late in his life he still had a soft spot for his punk music and Sherbert in particular. “My life was on the skids, and Like Flies on Sherbert was a summation of that period,” he said years later. “I like that record a lot. It’s crazy but it’s a positive statement about a period in my life that wasn’t positive.”

Ironically, given that it’s the debut solo album of a man who’d come to be considered a songwriting genius, Sherbert contains mostly covers (thought radically reimagined ones, from the likes of A.P. Carter and Ernest Tubb) and the few originals that appeared on it (“Rock Hard,” “Hey! Little Child”) would be the last songs Chilton would write for the next six years. In the meantime, Chilton surprised some people by joining the raucous avant-garde band Panther Burns, playing guitar in the shadow of charismatic frontman Tav Falco. (When he was in Panther Burns, Chilton went by playfully self-abnegating alter egos: LX Chilton eventually morphed into Axel Chitlin.)

“Ever since I’ve been playing music professionally I’ve been up front, and there’s been all this pressure,” he said. “I always wanted to be a guitar player for somebody for a while. It’s difficult to be entertaining, and if you’re really interested in playing music—which I am—you want some time where you can play music rather than when you’re out front.”

But he knew enough to know he had some internal work to do at this time, and that it would be impossible for him to get healthy while continuing to play the role of on-the-edge frontman and songwriter. “I feel like there’s a lot of character growth that I can do now, rather than writing songs,” he told a journalist around the time he left Panther Burns, in the early ’80s. A new generation of on-the-rise musicians like the Replacements and R.E.M. were by then discovering and deifying him. But for Chilton, moving away from his past was, in its own way, an act of self-preservation.

There’s a part when everyone in the Big Star story either dies, finds Jesus or opts for the “geographical cure,” moving someplace to clean up and start anew. Alex moved to New Orleans in 1982, when he was 31. He hardly knew anyone in town. “My mother said that Alex was the only person she knew who chose New Orleans as a place to get away from drugs and booze,” his sister Cecelia told George-Warren. He found a cheap apartment, a used record player at a local Goodwill, and a job as a dishwasher at a restaurant, where he’d work for the next year and a half. “He ended up scrubbing the big pots and pans,” his friend Vernon Richards recalled. “They later tried to get him to go to the Goodwill store and buy a tuxedo and become a waiter. They told him he’d make a lot more money, but he knew enough about it then that he liked scrubbing those pots and pans because nobody messed with him. So he turned down making some money as a waiter.”

Some people find this part of the story unbearably sad: Right at the moment indie rock was becoming a viable subculture, Chilton was holed up in a kitchen washing other people’s dishes. I have come to see in it a kind of grace. Early money and early fame had by then taught him that they weren’t worth chasing. In the next few years he’d find work trimming trees, mopping floors, and eventually playing in a bar cover band for $20 a set, a few afternoons a week. Chilton was, in George-Warren’s telling, a kind of “human jukebox … the tables had a printed list of songs customers would request the band to play.”

“It was the saddest, lowest joint on the street in those days,” he said later. “It was really fun, and in a way, that was the best time in my life.” One of the only records Chilton owned in those days was a copy of Chet Baker Sings, which his father owned when Alex was a kid. His favorite song was “Look For the Silver Lining.” Baker’s version didn’t include the second verse, but when Judy Garland sang it, she did:

As I wash my dishes, I’ll be following a plan

Till I see the brightness in ev’ry pot and pan

I am sure this point of view will ease the daily grind

So I’ll keep repeating in my mind Look for the silver lining, whene’er a cloud appears in the blue

By 1987, Chilton was once again writing songs and playing shows, having just released the album High Priest. He had not yet heard “Alex Chilton,” the Replacements song that had just been released on the band’s second major label record, Pleased To Meet Me. When the Replacements’ manager finally played it for Chilton, according to George-Warren, “he remembered Alex bracing himself before listening but then seeming relieved at what he heard.” Westerberg calls him an “invisible man who can sing in a visible voice,” and the song is a kind of alternate history wherein his band’s musical hero gets his due: “Children by the million sing for Alex Chilton when he comes ‘round / They sing, I’m in love. What’s that song? I’m in love with that song.”

I have long found the work Chilton made in the late ’80s and early ’90s more difficult to embrace than the work he inspired. (Teenage Fanclub’s fantastic 1991 album Bandwagonesque, for example, is sometimes jokingly referred to as Big Star Fourth.) The clean, rootsy sounds of High Priest and its predecessor, Feudalist Tarts, received raves from critics: Two consecutive EPs he released, in 1985 and 1986, were voted the best of both those years in the Village Voice’s annual Pazz & Jop critic’s poll. It’s hard to imagine that had nothing to do with the belated reappraisals of the Big Star records, which by then came to be known as cult masterpieces.

The new collection of his selected ’80s songs, From Memphis to New Orleans, does help put this period in context. Though they don’t have the panoramic ambiance of the Big Star records or the bratty abandon of Sherbert, songs like the bluesy “Lost My Job” or the sweetly content “Paradise” feel like a summation of the wider swath of Chilton’s musical fandom—all the way back to the days when his late older brother was turning him onto rock ’n’ roll. One of the best songs, “Underclass,” makes good on that connection Chilton once noted between ’50s rock and ’70s punk: “It’s a gas to be a member of the underclass,” he sings, while his guitar’s dirty, low-end distortion rumbles below like a GTO engine.

As ever, money and fame had some cosmic jokes in store for Chilton during the last third of his career, as two Big Star songs boomeranged back into public consciousness to make him the kind of cash they should have in the first place. In 1986, the Bangles covered “September Gurls” on their blockbuster album Different Light—and so Chilton found himself collecting handsome royalties on the record that featured “Walk Like an Egyptian.” Then, about a decade later, a Chilton fan working on the new Fox sitcom That ’70s Show suggested #1 Record’s “In the Street” as a possible theme song. Cheap Trick recorded an exuberant cover that anyone who’s seen more than 2 episodes can probably shout by heart. Chilton used the money to buy a piano for his small house in Treme, where he’d live the last decade of his life.

Sometimes the songbook giveth; sometimes the songbook taketh away. Chilton’s career stretched long enough to see both sides of that exchange. There is a simple, earnest sweetness to the arrangements on Songs From Robin Hood Lane, most of which was recorded in the early 90s and a few tracks of which also appear on his 1993 album Clichés. A highlight is his hushed, gently finger-picked rendition of “My Baby Just Cares for Me,” which somehow bridges the gap between the lo-fi ache of “Thirteen” and the accomplished elegance of Nina Simone. Another new addition is a straightforward crooner’s take on a standard he loved deeply enough to turn it into a kind of late-in-life mantra, “Look for the Silver Lining.”

Even if I can’t see myself returning to it as often as Radio City, there is a warm charm to this material. Perhaps, in retrospect, what is so moving about Chilton paying such plaintive homage to the American songbook is the knowledge that he is now widely seen as having made his own contributions to it. Songs like “Thirteen,” “September Gurls,” and “In the Street” have become, in their own way, modern-day standards, floating through the pop ether (Even the Monkees, on their bestselling Christmas album, covered “Jesus Christ.”) That these songs are better known than their creator might have given the self-effacing Chilton some comfort, but it would be a mistake to see them as something completely separate from his one-of-a-kind life, his panoramic musical perspective, his uncanny talent. One of the first songs Chilton chose to cover after leaving the Box Tops in 1970, newly dizzy with creative freedom, was the Rolling Stones’ “The Singer Not the Song.” Perhaps Chilton came to see that music’s power was both of those things, or even neither of them: an invisible man who could sing in a voice you could see.