The track was recorded at American Sound Studio in Memphis in a session produced by Dan Penn. Previously a musician and engineer at FAME Studios, Penn had been hired as production assistant by American Sound's owner Chips Moman, who Penn felt was shutting him out as a collaborator. Penn recalls: "Finally, I just told [Moman]...'Look, we can't produce together...I think I can produce records [alone]...But I do need somebody to cut. Give me the worst one you got'." Moman suggested Penn record a local five man outfit who had been pitched to him by disc jockey Ray Banks (Penn - "Chips was just graspin'. He'd never heard [the group]") and also passed on to Penn a demo tape of songs cut by his friend Wayne Carson Thompson which included "The Letter". Thompson's father dabbled in songwriting and would suggest ideas to his son, who had written "The Letter" after his father had suggested: "Give me a ticket for an aeroplane" as a potential opening line for a song. Penn met with some of the members of the group - who were eventually dubbed the Box Tops - "and told them to pick anything they wanted from this tape [by Thompson], but make sure that we do 'The Letter'" which Penn considered the one outstanding song.
The session for "The Letter" began at 10 o'clock on a Saturday morning and took over thirty takes wrapping at either three or five o'clock that afternoon. Penn met Box Tops' vocalist Alex Chilton for the first time at the session: "I coached him a little...told him to say 'aer-o-plane", told him to get a little gruff, and I didn't have to say anything else to him". (Composer Thompson, who says he played guitar at the session, was thrown by Chilton's vocal, having imagined the song being sung in a higher key.) Penn - "[Chilton] picked it up exactly as I had in mind, maybe even better. I hadn't even paid any attention to how good he sang because I was busy trying to put the band together...I had a bunch of greenhorns who'd never cut a record, including me...I borrowed everything from Wayne Thompson's original demo - drums, bass, guitar. I added an organ with an 'I'm a Believer' lick." Penn added the sound of an airplane take-off to the track by recording off of a special effects record played in an office adjacent to the recording studio. When the track was previewed for Chips Moman he suggested the take-off sounds be excised, to which Penn responded: "Give me that razor blade right there...[and] I'll cut this damn tape up! The airplane stays on it, or we don't have a record."
Augmented with strings and horns (arranged by Mike Leach), the track was picked up by Larry Uttal of Bell Records who released it on the subsidiary Mala label in July 1967 to reach #1 that September. Retaining the #1 position for a total of four weeks, "The Letter" was ranked as the #1 hit of 1967. The track also gave the Box Tops an international hit charting in Australia (#4 for six weeks), Austria (#9), Belgium (Flemish Region) (#2), Chile (#1), Denmark (#7), France (#2), Germany (#5), Greece (#2 foreign release), Ireland (#11), Israel (#1), Malaysia (#4), New Zealand (#4), the Netherlands (#3), Norway (#1), Poland (#1), South Africa (#4), Spain (#9) and Sweden(#2). The Box Tops also reached #5 in the UK, besting a cover by the Mindbenders which reached #42.
The Box Tops sold more than one million copies of "The Letter" and received a gold disc. At only 1 minute, 58 seconds, "The Letter" is one of the shortest songs to top the chart. Singer Alex Chilton was only 16 years old when recording "The Letter".
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In November 1968 the Arbors recorded an easy listening style version of "The Letter" in a session at Record Plant Studios in New York produced by Roy Cicala and Lori Burton; the session was arranged and conducted by Joe Scott. Released on CBS Records Date label, the track reached #20 in the spring of 1969, also ranking at #26 on the Easy Listening charts and #24 in Canada. "The Letter" was also recorded in 1969 by the Ventures, appearing on their album Hawaii Five-O.
"The Letter" returned to the U.S. Top Ten in June 1970 via a single release of Leon Russell's blues-rock reinvention of the song as performed by Joe Cocker and featured on the Mad Dogs and Englishmen live album recorded that March at the Fillmore East. Cocker's revival was also a chart item in Australia (#27), Canada (#7), France (#48), the Netherlands (#27) and the UK (#39).
In 1978 "The Letter" became a disco hit for Deborah Washington reaching #13 on the Billboard dance chart in tandem with Washington's remakes of "Standing in the Shadows of Love" and "Fire" - all three tracks were taken from Washington's Any Way You Want It album. Amii Stewart also recorded a disco version of "The Letter" which was released on a single with "Paradise Bird" to become a double sided chart entry in the UK at #39 in 1980. Stewart's "The Letter" also reached #31 in France, becoming the fourth version of the song to appear on the French charts, following the Box Tops and Joe Cocker versions and also a translated version by Herbert Léonard entitled "Une Lettre" which charted December 1967–January 1968 with a #82 peak.
Ranked by Rolling Stone at #363 on the magazine's list of the 500 Greatest Songs of All Time, "The Letter" was reported in July 1979 to have been recorded in over 200 different versions. Among the artists who have recorded the song are Charly García, Bachman–Turner Overdrive, the Beach Boys, Eva Cassidy, Shaun Cassidy, Classics IV, Bobby Darin, John Davidson, Don Fardon, Al Green, Ellie Greenwich, Sonny James,Robert Knight, Brenda Lee, Trini Lopez, Arjen Anthony Lucassen, Barbara Mandrell, Peter Tosh, by then a member of Wailing Wailers did a cover renamed "Give Me a Ticket" on the album "Selassie is the Chapel"Melanie, the Moments, Lou Rawls, Johnny Rivers and Dionne Warwick. Romanian singer Gil Dobrică recorded a Romanian language version in 1987, Scrisoarea (The letter). It was also covered during the ninth season of American Idol by winner Lee DeWyze. In 2003, a cover by A-Teens appeared on their album New Arrival. In 2008, a cover by Neal Morse, Randy George and Mike Portnoy appeared on the special edition of Neal Morse's album "Lifeline".
On the third album by Seasick Steve (I Started Out with Nothin and I Still Got Most of It Left), there is a bluesrock cover of "The Letter". It was released on 29 September 2008.