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.
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