Chilton grew up in a musical family; his father, Sidney Chilton, was a jazz musician. A local band recruited the teenager in 1966 as their lead singer after learning of the popularity of his vocal performance at a talent show at Memphis' Central High School; this band was (Ronnie and) the Devilles, later renamed The Box Tops. The new group recorded with Chips Moman and producer/songwriter Dan Penn at American Sound Studio and Muscle Shoals' FAME Studios.
As lead singer for The Box Tops, Chilton enjoyed at the age of 16 a number-one international hit, "The Letter". The Box Tops went on to have several other major chart hits, including "Neon Rainbow" (1967), "Cry Like a Baby" (1968), "Sweet Cream Ladies, Forward March" (1969), and "Soul Deep" (1969). Aside from the hits "The Letter", "Neon Rainbow", and "Soul Deep", all written by Wayne Carson Thompson, many of the group's songs were written by Penn, Moman, Spooner Oldham, and other top area songwriters, with Chilton occasionally contributing a song. By late 1969, only Chilton and Guitarist Gary Talley remained from the original group, and newer additions replaced the members who had departed. The group decided to disband and pursue independent careers in February 1970.
After deciding against pursuing a higher education at Memphis State University, Chilton began performing as a solo Artist, maintaining a working relationship with Penn for demos. During this period he began learning guitar by studying the styles of guitarists like Stax Records great Steve Cropper, recording his own material in 1969–70 at Ardent Studios with local Musicians like Producer Terry Manning (who had worked with Chilton as an Engineer on The Box Tops' recordings) and Drummer Richard Rosebrough, and producing a few local blues-rock acts. His 1970 recordings and productions from that time frame were released years later in the 1980s and 1990s on albums like Lost Decade (New Rose Records) and 1970 (Ardent Records).
After a period in New York City, during which Chilton worked on his guitar technique and singing style (some of which was believed to have been influenced by a chance meeting with Roger McGuinn at a friend's apartment in New York when Chilton was impressed with McGuinn's singing and playing), Chilton returned to Memphis in 1971 and co-founded the power-pop group Big Star, with Chris Bell, recording at Engineer John Fry's Ardent Studios. Chilton and Bell co-wrote "In The Street" for Big Star's first album #1 Record, a track later covered by Cheap Trick and used as the theme song of That '70s Show.
The group's recordings met with little commercial success but established Chilton's reputation as a rock singer and songwriter; later alternative music bands like R.E.M. and The Posies would praise the group as a major influence. During this period he also occasionally recorded with Rosebrough as a group they called The Dolby Fuckers; some of their studio experimentation was included on Big Star's album Radio City, including the recording of "Mod Lang". Rosebrough would occasionally work with Chilton on later recordings, including Big Star's Third album and Chilton's 1975 solo record Bach's Bottom.
Moving back to New York in 1977, Chilton performed as "Alex Chilton and the Cossacks" with a lineup that included Chris Stamey (later of The dB's) and Richard Lloyd of Television at venues like CBGB, releasing an influential solo single, "Bangkok" (b/w a cover of the Seeds' "Can't Seem to Make You Mine"), in 1978. This period learning from the New York CBGB scene marked the beginning of a key change for Chilton's personal musical interests away from multi-layered pop studio recording standards toward an animated punk and traditional pop-influenced performance style often recorded in one take and featuring few overdubs. There he made the acquaintance of The Cramps, a formative psychobilly ensemble. He brought them to Memphis, to which he had moved back to by April 1978, where he produced the songs that would appear on their Gravest Hits EP and their Songs the Lord Taught Us LP.
In 1979, Chilton released, in a limited edition of 500 copies, the album Like Flies on Sherbert. Produced by Chilton with Jim Dickinson at Phillips Recording and Ardent Studios, it features his own interpretations of songs by artists as disparate as the Carter Family, Jimmy C. Newman, Ernest Tubb, and KC and the Sunshine Band, along with several originals. While criticized by some as a druggy mess, this album is considered by many to be a lo-fi masterpiece. Sherbert—which included backing work from such notable Memphis Musicians as Rosebrough, Drummer Ross Johnson, and Chilton's longtime on-again/off-again companion, Lesa Aldridge—has since been reissued several times. Beginning in 1979 Chilton also co-founded, played guitar with, and produced some albums for Tav Falco's Panther Burns, which began as an offbeat rock-and-roll group deconstructing blues, country, and rockabilly music.
Touring and recording as a solo Artist from the late 1980s through the 1990s with bassists Mike Maffei, John S. McClure (later to become a professor of Divinity at Vanderbilt University), and Ron Easley, and with drummers Doug Garrison and, from 1993 on, Richard Dworkin (who also played for many years with the jazz group The Microscopic Septet), Chilton gained a reputation for his eclectic taste in song covers, guitar work, and laconic stage presence. Writing about a live performance in the New York Times, critic Peter Watrous said of Chilton that "He's a soul and blues guitar connoisseur; he chooses his guitar licks as carefully as he does the blues songs he covers, and during his solos, a listener heard a history of soul and blues guitar." Watrous went on to say of the show that "Irony flowed over everything, and it was hard to tell exactly what Mr. Chilton was after, except perhaps a little fun."
Chilton toured briefly in 1981 as a solo act, backed by a trio of Musicians who played at different times with Tav Falco's Panther Burns: Guitarist Jim Duckworth, Bassist Ron Easley (with whom Chilton would tour and record with extensively in the 1990s and 2000s), and Drummer Jim Sclavunos. The group played a string of shows in the fall in Chicago, Washington D.C., Philadelphia, New York, and New Jersey; this would be Chilton's last tour for three years.
Chilton moved to New Orleans in 1982, where he spent much of 1982 and 1983 working outside music, washing dishes at the Louis XVI Restaurant in the French Quarter, working as a janitor at the Uptown nightclub Tupelo's Tavern, and working as a tree-trimmer. He resumed playing with Panther Burns in 1983. His new association with New Orleans jazz Musicians (including Bassist René Coman) marked a period in which he began playing guitar in a less raucous style and moved toward a cooler, more restrained approach, as heard in Panther Burns's 1984 Sugar Ditch Revisited album, produced by Jim Dickinson. He moved back into playing music full-time in the summer of 1984, when he and Coman began a four-month stretch playing in a cover band called The Scores, working in four-hour shifts at the Bourbon Street tourist bar Papa Joe's, and taking requests from a printed list of songs placed on the customer tables.
After the cover-band job ended, Chilton contacted a booking agent recommended to him by The dBs Drummer Will Rigby, and soon had a handful of club gigs lined up in New York, New Jersey, and Boston for the fall of 1984. He stopped playing regular gigs with Panther Burns and formed a trio with the group's Bassist, Coman, and Drummer Joey Torres to play his out-of-town bookings. At this point, his career was effectively relaunched, and for the next 25 years, Chilton sporadically led a three-piece touring band (augmented by Saxophonist Jim Spake in 1989 and 1990), recorded studio and live solo records for several independent record labels, and reunited with versions of his previous bands The Box Tops and Big Star for brief tours and recordings.
At the outset of this period, while in New York in 1985 to play a booking at the Danceteria club, Chilton was connected through a Journalist with Patrick Mathé, founder of the Paris-based record label New Rose. Chilton's Business relationship with Mathé would last the rest of his life, and New Rose (and its successor label, Last Call Records) released in Europe much of Chilton's solo work from 1985–2004, as well as a 1998 Box Tops reunion album. In the U.S., Chilton's solo releases were released by the Big Time, Razor & Tie, Ardent, and Bar/None record labels. In 1985, Chilton began working with Memphis jazz Drummer Doug Garrison (who had played music with Chilton's father Sidney in a big band), and his trio continued touring and began to record as well. Six songs were recorded at Ardent Studios for the 1985 EP Feudalist Tarts, three originals joined by songs from the catalogs of Carla Thomas, Slim Harpo, and Willie Tee. In 1986 Chilton followed this with a second EP, No Sex, which contained three more originals, including the extended mood piece, "Wild Kingdom", a song highlighting Coman's jazz-oriented, improvisational bass interplay with Chilton.
In 1986, The Bangles released their second LP, Different Light, which contained a cover version of Chilton's Big Star song "September Gurls". Royalties from this version allowed Chilton, who had struggled financially since leaving The Box Tops, to buy his first new car since his Box Top days, and a piece of rural land near Hohenwald, Tennessee, where he planned to build a small house. The following year, his visibility increased in the alternative rock scene when he was the subject of the song "Alex Chilton" by American rock band The Replacements on their album Pleased to Meet Me, on which Chilton was a guest musician playing guitar on the song "Can't Hardly Wait".
With 1987's High Priest, Chilton released his first full-length LP in eight years, for which he served as Producer and wrote four new songs. He was given a $21,000 recording budget by his European and U.S. record labels (New Rose and Big Time, respectively) which allowed him to augment his band on various songs with a three-piece horn section, backup Singers, piano, keyboards, and rhythm guitar. He was also able to continue the genre-mixing he had started with Like Flies on Sherbert by including soul, blues, gospel, and rock songs on the same record. He ended the album with a cover of "Raunchy", his instrumental salute to Sun Records Guitarist Sid Manker, a friend of his father from whom he'd once taken a guitar lesson; this song was also a standard in his early Panther Burns repertoire. High Priest also included other covers like "Nobody's Fool", a song originally written and recorded in 1973 by his old mentor and Box Tops Producer Dan Penn. While his solo career was continuing to pick up momentum, Chilton was also singing Box Tops songs during 1987 with a package tour of 1960s artists including Peter Noone, Ronnie Spector, and Question Mark & the Mysterians.
In 1990 and 1991, Chilton took time off from touring and recording to live during the warm months in a tent on his land in rural Tennessee and work on clearing trees and framing his planned house, a project he was never to complete. In 1993, Chilton recorded Clichés, an acoustic solo record of jazz and pop standards, in New Orleans' Chez Flames studio with Producer Keith Keller. The record was inspired by a short solo acoustic tour of the Netherlands featuring Chilton, alternative country luminary Townes Van Zandt, and several other Musicians in January, 1992. Chilton's final two studio albums featured his band and continued his pattern of mixing together songs from pop, soul, blues, gospel, R&B, swing, and country music. A Man Called Destruction (1995), like High Priest, featured a mix of covers and originals and an expanded band that included horns, keyboards, and occasional backup Singers, and was released in the U.S. on the relaunched Ardent Records label. Chilton took an enlarged edition of his band on Late Night with Conan O'Brien in July 1995 to promote the album, playing the song "Lies". This was Chilton's second appearance on national television in less than a year; in October 1994, he appeared on The Tonight Show with Jay Leno with the reformed Big Star. Chilton's final solo studio record, Loose Shoes and Tight Pussy (1999), featured only his trio, and was named after an old off-color joke made infamous in 1976 by Politician Earl Butz. Chilton released one more album as a solo Artist, the 2004 CD Live in Anvers, which featured him playing a show in Belgium with a pick-up band of European Musicians.
Big Star's October 29, 1994, performance, their only known show to be professionally filmed in its entirety, was released in November 2014 by Omnivore Recordings as Live in Memphis. According to Mojo, the DVD documents how Big Star's 1990s lineup defied expectations and endured for another 16 years: "Chilton's musicality is mesmerising as he drives the band.... Alternating between lead and rhythm, he plays with a mix of laser focus and utter insouciant cool."
In 1996, Chilton regrouped in Memphis with original Box Tops members Danny Smythe, John Evans, Bill Cunningham, and Gary Talley, and the following year they recorded Tear Off!, the group's final record with Chilton. The album, which was recorded primarily at Easley Recording Studios in Memphis, was released in Europe in 1998. Chilton subsequently toured with the original group annually. Chilton had toured Europe in 1991 with a version of the band, and had sung Box Tops material as a featured singer in oldies package tours during the 1980s and 1990s. After Chilton's death, the Box Tops were to reform again in 2015 with Guitarist Gary Talley as lead vocalist.
In 1998, the Alex Chilton / Chris Bell song "In the Street" (from the first Big Star album) was chosen as the theme music for the U.S. television series That '70s Show at the suggestion of Chilton's friend and occasional touring partner Ben Vaughn. Vaughn was working for the series at the time, and oversaw a new recording of the song by singer Todd Griffin and a group of Los Angeles studio musicians; in subsequent seasons, a version recorded by the band Cheap Trick would be used.
Chilton toured and recorded less frequently in his final decade, choosing to spend more of his time at home in New Orleans. In 1995, Chilton had purchased a 19th-century center-hall cottage in the Tremé neighborhood for $13,000, and he enjoyed working on his house and practicing Scott Joplin rags on his piano (an instrument he was to lose in Hurricane Katrina). "Thanks to his low overhead, Chilton subsisted [during the 2000s] on periodic Big Star, Box Tops and solo gigs augmented by modest publishing income....He saw little reason to hustle more than was necessary to make ends meet and travel, a favorite pursuit" wrote New Orleans Journalist Keith Spera in a profile published after Chilton's death. Chilton was present at his home in New Orleans during Hurricane Katrina and evacuated by helicopter on September 4, 2005. In 2009, he remarried. Chilton's last studio projects included playing bass on Cristina Black's The Ditty Session, and producing tracks by Guitarist and singer "Johnny J." Beninati, a former member of the New Orleans rockabilly group The Blue Vipers. Chilton's final live performance was in New Orleans on January 24, 2010, where he participated in benefit show for Haitian earthquake victims.
Chilton was taken to the hospital in New Orleans on Wednesday, March 17, 2010, complaining of health problems, and died the same day of a heart attack. Chilton had experienced at least two episodes of shortness of breath in the week prior to his fatal heart attack, though he did not seek medical attention in part because he did not have health insurance. He was survived by his wife, Laura, a son, Timothee, and a sister, Cecilia.