Last November 18th, at the Brooklyn Masonic Temple in New York, Alex Chilton played what turned out to be his last show with the reunited version of his early-Seventies power-pop band, Big Star. It was also one of his best. You could tell by Chilton's smile, a wide gleam that the Memphis-born singer-guitarist flashed at his bandmates – original drummer Jody Stephens and singer-instrumentalists Jon Auer and Ken Stringfellow, both of the Posies and members of Big Star since 1993 – during the adoring applause for songs such as "The Ballad of El Goodo," a pearl of adolescent-pining harmonies from the 1972 LP #2 Record, and the heavy-jangle delight, "Back of a Car," on 1974's Radio City. Those albums were dismal sellers when they came out. But in Brooklyn, they were greeted like classic-rock gospel by alternative-rock and indie-generation fans who knew many of the lyrics by heart.
Four months later, on March 17th, Chilton died of a heart attack in New Orleans – where he had lived since the early Eighties – as his wife, Laura Kersting, rushed him to a hospital. He was 59.
"That smile, with Alex, was so revealing," Stephens says now of that night in Brooklyn. "There was an honesty there that Alex would never speak. But he would show it on his face." In the dressing room after the show, Stephens remarked to Chilton "what an incredible audience it was." Chilton didn't say a word, Stephens recalled: "He just smiled and shook his head up and down."
Chilton could go on for hours, with strangers backstage, on topics that interested him: astrology, classical music, landscaping in 19th-century France, the history and politics of the South during Reconstruction. But "he wasn't good at receiving compliments," says John Fry, who founded the Memphis studio, Ardent, where Big Star made their records and who engineered many of those sessions. "Somebody would praise something on those records, and he'd shrug and say, 'Well, there wasn't much to that.'"
"Alex found some of the Big Star songs really embarrassing," Stringfellow says. "For him, it was like having your old diary on display. But that Brooklyn show was a real step up. He seemed like, 'If people are this into it, how can you hate it?'"
Chilton died with ironic timing, on the first day of the SXSW Music and Media Conference. Big Star were already scheduled as a featured act at the festival, with a panel discussion on their music and influence and a headlining set on the final night, March 20th, at the club Antone's. Instead, the panel became a memorial celebration of Chilton's life, and Stephens, Auer and Stringfellow turned the Antone's show into an exhilarating wake, with guest performances by acolytes and friends such as Chris Stamey, Evan Dando, John Doe of X and original Big Star bassist Andy Hummel, in his first appearance with the group since 1973.
"We rose to a difficult occasion, but I can't say it was enjoyable," Stringfellow confesses. When he sang Chilton's lovesick chorus in "Feel," from #1 Record ("I feel like I'm dying/I'm never gonna live again"), "it was like driving nails through my heart."
The stereotypical rock-star career goes like this: years of struggle and obscurity; then critical acclaim and just reward. Chilton lived that arc in reverse: instant fame with the Memphis pop-soul band the Box Tops; followed by commercial frustration, personal trials and intense cult love in his Big Star years; and finally a long life under the mainstream radar. Chilton, in fact, defined overnight success. "The Letter," his 1967 debut with the Box Tops, recorded when Chilton was 16, was Number One for four weeks. The Box Tops churned out white-R&B hits through 1968 and '69, including "Cry Like a Baby," "I Met Her in Church" and "Soul Deep," driven by Chilton's precociously gritty, sexually heated singing. That voice shocked even those close to him. His older sister Cecelia says their mother, Mary, joked with friends that she "never even heard him sing in the shower."
Formed in Memphis in 1971 with Stephens, Hummel and singer-guitarist Chris Bell, Big Star brought out Chilton's true voice – cleaner, brighter and dramatically vulnerable, framed in compelling tangles of Beatlesque guitars and adolescent choral sighs. The combination of eccentric musical complexity and direct romantic engagement in Chilton's teenage-rebel melodrama "Thirteen," on #1 Record, and his Radio City lust nugget "September Gurls" eventually made Big Star a pop beacon for post-punk bands like R.E.M., the dB's and the Replacements. ("I never travel far/Without a little Big Star," the Replacements' Paul Westerberg would sing in his 1987 tribute, "Alex Chilton.")
It was, at the time, a perfection in vain. The two albums never charted. Bell quit after #1 Record; Hummel split after Radio City. In 1974, Chilton – drinking heavily and in a turbulent relationship – made 3rd with Stephens. A record of purposely twisted majesty, brutally candid in its rage and hurt, it was not released until 1978, after Chilton and Stephens had put Big Star to rest, "3rd was ahead of its time, the same way Brian Wilson's Smile was," says Stamey, who was in the dB's and played with Chilton at the turn of the Eighties. "If you listen to independent releases of 10 years ago, 3rd seems very contemporary."
But for the past three decades, Chilton chose the life of a reluctant legend. In 1982, he quit music entirely for a time, moving to New Orleans and taking a job washing dishes at a restaurant in the French Quarter. He also turned away from alcohol and drugs. "It was a cleansing period for Alex, a purging," says Stephens. By the time he and Chilton started Big Star again in 1993, Chilton was a spare drinker – "I saw him have one beer in the first five years I was in Big Star," Stringfellow says – and only had two major vices: cigarettes and pot.
In New Orleans, Chilton lived modestly but comfortably on tour income and publishing royalties, including a windfall from Cheap Trick's cover of "In the Street," used as the opening theme for That '70s Show. Chilton made occasional solo records and performed – on his own, with Big Star and, in recent years, a reunited Box Tops – only when it was a pleasure. "Alex didn't do things he didn't want to do," says Stephens. "He couldn't fake having a good time. He couldn't be bothered."
But Chilton was no contrarian. He just refused to be anything but honest, in his songs or life. "The reputation was there," Stringfellow says, "and that rankled him. Alex was blunt. When you asked him a question, he'd go, 'No.' A lot of people go, 'I'll think about that. I'll get back to you.' And they never call you back. You never got that from Alex."
At the SXSW panel, Stamey recounted something Chilton once told him from his dishwashing days. A co-worker at the restaurant had caustically remarked to Chilton, "Yeah, Alex, you're right, and the rest of the world is wrong."
"You know," Chilton told Stamey, "I think he was really on to something."
William Alexander Chilton was born in Memphis on December 28th, 1950, the youngest of Sidney and Mary Chilton's four children. Sidney was a manufacturers' representative and an avid jazz musician. When the family moved from its first home, in a neighborhood called Sherwood Forest (the Chiltons lived on Robin Hood Lane), to a large stone house in the Midtown section of Memphis, Sidney hosted jam sessions with friends while Mary ran an art gallery on the first floor. Cecelia, 10 years older than Alex, remembers her brother as "a sweet kid. He would make popcorn for my teenage friends when they would come over."
Alex got his first guitar when he was 14 and was soon in his first working band, the Jynx, with his future Big Star partner Chris Bell and Bill Cunningham, who later played bass in the Box Tops. "We were a hot little band," Cunningham says, "but Alex's voice just propelled us."
From the start, Chilton had a forceful way of expressing his likes and dislikes. "He was perceptive and could see clearly through any phoniness," Cunningham says. "He always expressed himself for clarity, but with brutal honesty." Cunningham remembers missing one of his backing-vocal parts during a Box Tops gig. Chilton walked behind him and kicked Cunningham in the ass with one of his pointed Beatle boots. "It hurt, too," Cunningham says. "But it was effective. I never forgot to sing that vocal part again."
Chilton was just as direct in his gratitude. Session musician Spooner Oldham, who played keyboards on Box Tops records and co-wrote songs for the group with its producer Dan Penn, says he met Chilton for the first time after a grueling all-night writing session for "Cry Like a Baby." When Oldham and Penn played their demo of the song for Chilton, "Alex looked at me with a big smile on his face, reached out his hand and said, 'Thank you.' He was genuine that way." Then, Oldham adds, "he went into the session and sang like a bird."
After the Box Tops collapsed at the end of 1969, Chilton made his first solo album at Ardent, an effort that went unreleased at the time despite interest from Atlantic Records and the Beach Boys' label, Brother (Chilton got friendly with Carl and Dennis Wilson when the Box Tops toured with the Beach Boys). Issued in 1996 as 7570, the record includes "Free Again," a country-pop gem that, like many of Chilton's later songs, was rooted in painful experience. "Well, I made a mistake/Thought I could settle down," he sang, alluding to a brief marriage when he was 17. "That was about the time his divorce was becoming final," says John Fry. "He was feeling free of the Box Tops' constraints but also in his personal life." (Chilton is survived by a son, Timothee, from that marriage.)
During a trip to New York, where he played solo acoustic shows, Chilton ran into Bell, who was shopping tapes of his band Ice Water with Stephens and Hummel. The four were soon back in Memphis, polishing the songs for #1 Record in a small practice building next door to Ardent. "Alex and Chris were the leaders," says Stephens. "Chris had an overall vision for #l Record, but Alex had an opinion about things, usually about something being done a little too carefully." Fry says Bell "looked for perfection in everything. Alex wanted to get it right but didn't want to fret about it." (Bell died in 1978 in a car crash in Memphis, after releasing a legendary solo single, "I Am the Cosmos.")
Today, Stephens looks back at 3rd with amazement and shock. "It was an emotionally raw period," he says. Chilton and Stephens were dating sisters – Chilton wanted to use Sister Lovers as a band name. But Chilton's romance was in constant turmoil, aggravated by his drinking and drug use. Stephens quotes the last lines of the song "Holocaust": "You're a wasted face/You're a sad-eyed lie/You're a holocaust." That, Stephens says, "was an emotional atom bomb to drop on someone."
3rd and Chilton's 1980 solo album, Like Flies on Sherbert – an equally confounding mix of primitivist R&B and poignant heartbreak (the original "My Rival") – sealed Chilton's reputation in the punk era as brilliant damaged goods. In fact, during a late-Seventies spell in New York, playing in punk clubs, Chilton "was in great shape," says Stamey. "By the end of his tenure there, he felt like he should get out, because there were too many people willing to buy him drinks."
By 1982, he had split New York, eventually settling in New Orleans. "My mother always said that Alex was the only person she knew who chose New Orleans as a place to get away from drugs and booze," Cecelia says, laughing. But Chilton enjoyed the relaxed pace of living and the lack of music-industry pressure there. "He wanted a clean start," says Rene Coman, a local bassist who started playing with Chilton shortly after he came to New Orleans. "It took a long time before he played any Big Star stuff, or even mentioned it."
In the early Nineties, Chilton bought a 19th-century cottage in the Treme section of New Orleans. His mostly black neighbors marveled at the sight of him cutting his grass with a push mower. Chilton did not use e-mail (Stringfellow did Big Star tour business with Chilton via phone and a fax machine at a nearby Kinko's) and took long bike rides around town. "He cultivated relationships with everyone," says Kersting, a longtime acquaintance who married Chilton last August. "Everyone that passed by, he would say hello and have a conversation." That often included impromptu astrological readings.
At one point in the Eighties, Chilton played in a cover band on Bourbon Street, taking requests, mostly R&B standards. In recent years, he enjoyed performing at the annual Ponderosa Stomp revues – as a sideman for soul heroes like Brenton Wood. Chilton rarely played under his own name in New Orleans. "He wanted other people to have those slots at the clubs," Kersting says. "He didn't want to gain from New Orleans. He wanted to give."
Chilton's last live show, on January 24th, was in that spirit: a benefit for Doctors Without Borders at a New Orleans gallery called the Big Top. Chilton declined to rehearse with his trio or write a set list. "He said, 'We'll wing it,'" says Anthony Donado, who organized the benefit and played drums. "I guess that's all you could ask of Alex. He liked music on the edge."
This story is from the April 15th, 2010 issue of Rolling Stone.