1967 No. 1 Classic, Ranked Among 'Greatest Songs of All Time,' Was Sung by a 16-Year-Old
You know a song is a true hit when it's a major success for more than one artist or band. A perfect example? "The Letter," which shot to the top of the charts when it was originally released by The Box Tops in 1967, then became one of Joe Cocker's most popular and beloved covers just a few years later in 1970. Not bad for a song that was sung by a teenager the first time around.
Though he would later become known as the frontman for the critically acclaimed band Big Star, Alex Chilton was just a 16-year-old newcomer when he recorded "The Letter" as lead singer of The Box Tops. The singer didn't sound like a kid on the track, of course; in fact, his vocals are particularly gruff and soulful. According to Chilton, that was a result of producer Dan Penn's direction.
"[He] coached me pretty heavily on singing anything we ever did. In a lot of cases, it sounds more like him singing than it sounds like me," Chilton said later, per Rolling Stone, which ranked "The Letter" at #372 on their list of "500 Greatest Songs of All Time."
Just a few years after The Box Tops made "The Letter" a hit for the first time, Joe Cocker brought the song right back to the charts as a single from his iconic live album, Mad Dogs & Englishmen. This wasn't Cocker's first successful cover; his versions of "With A Little Help From My Friends" and "She Came In Through The Bathroom Window" by the Beatles made an impression on listeners, too...but his distinctive take on "The Letter" was Cocker's first top 10 hit in the U.S., peaking at #7 on the Billboard Hot 100.
A Billboard review of the song at the time praised the song's "blockbuster blues arrangement that has all the ingredients to up the number back in the Top Ten once again."
In 2025, the legendary 1971 concert film and documentary Mad Dogs & Englishmen made its premiere on YouTube, including two hours of tour footage from offstage and on. "The Letter" is one of the songs featured, in addition to "Feelin' Alright," "Delta Lady," and many others.
Copyright 2026 The Arena Group, Inc. All Rights Reserved
This story was originally published May 25, 2026 at 8:48 PM.