Alex Chilton, the singer and guitarist who had a No. 1 hit as a gravel-voiced teen with "The Letter" and went on to influence a generation of musicians through his work with Big Star, died Wednesday in New Orleans. He was 59.
The Memphis, Tenn., native died at a hospital, apparently of heart problems, said his longtime friend John Fry.
Chilton had his first taste of fame with the Box Tops, the band he and his friends started in Memphis. He was 16 but sounded much older when "The Letter," which opens with "Gimme a ticket for an aeroplane. Ain't got time to take a fast train …" hit the top of the charts in 1967. Their other hits were "Soul Deep" and "Cry Like a Baby."
But Chilton soon realized he didn't enjoy playing it straight, said Chips Moman, then his producer.
"He didn't want to do those kinds of songs we were doing. Sometimes that's more powerful than the money you receive for a hit record," Moman said.
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It was Chilton's work with a second Memphis band, Big Star, in the early 1970s that cemented his legacy as a pioneering voice for a generation of kids looking for something real in the glossy world of pop music.
The band was never a commercial success, but R.E.M. counted Chilton as an influence, the Replacements name-checked him with their 1987 song "Alex Chilton," and his band still provides a template for musicians today.
Chilton's influence was felt widely in the 1980s and 1990s, when a generation of listeners looked to songs like "Thirteen," "I'm in Love With a Girl" and "In the Street" (the theme song for "That '70s Show") because they captured teen angst perfectly and relayed sometimes-dark emotions that were universal.
Big Star's three 1970s albums all earned spots on Rolling Stone's list of the 500 greatest.
In addition to sporadic solo work, Chilton reformed Big Star with members of The Posies in the 1990s to tour and released "In Space" under the Big Star name in 2005.

