The Box Tops — “Trouble with Sam”: Brace for the Obscure (60s rock)! — January 15, 2026

THE GREATEST SONGS OF THE 1960s THAT NO ONE HAS EVER HEARD

1,846) The Box Tops — “Trouble with Sam”

“Trouble with Sam” “could [be] another song from the 1966-1970 English pop factories . . . . I have no basis for saying this, but I’d bet that Alex [Chilton] hated it. I don’t, because I like goofy pop confections.” (BeSteVenn, https://forums.stevehoffman.tv/threads/thank-you-friends-alex-chilton-chris-bell-big-star-box-tops-song-by-song.1202469/page-17)

Robert Pincus:

It’s a teenage tearjerker, and the lyrics are hopelessly adolescent. However, I love it, and I love it just as much as I did . . . when I was more in touch with the song’s sentiment. Vocally, it’s magnificent, and Alex sings pretty close to what I believe was his natural voice. The stereo imagery is fabulous. If the song makes you feel a little teary, don’t say I didn’t warn you.

https://positive-feedback.com/reviews/music-reviews/the-box-tops-cry-like-a-baby/

I also love it. I have no trouble with “Trouble with Sam”!

Some are more ambivalent: “It is really catchy — but feels underdeveloped, so the song is not quite the earworm that it seems to want to be. It’s screaming out for another section that never comes.” (intv7, https://forums.stevehoffman.tv/threads/thank-you-friends-alex-chilton-chris-bell-big-star-box-tops-song-by-song.1202469/page-17) It “foreshadow[s] the British Invasion style that [Alex] Chilton would employ with Big Star, but the melody lines and instrumentation lack the gritty authenticity found on ‘The Letter’.” (Steve Kurutz, https://www.allmusic.com/album/cry-like-a-baby-mw0000058519)

And then there is this sentiment: “This is barely half baked and Alex sounds like he couldn’t care less that Sam can’t remember his name”. (John Porcellino, https://forums.stevehoffman.tv/threads/thank-you-friends-alex-chilton-chris-bell-big-star-box-tops-song-by-song.1202469/page-17) 🤣🤣🤣

Steve Huey opens the Box Tops:

During their brief lifespan, the Box Tops earned a reputation as one of the best blue-eyed soul groups of the ’60s . . . . Today they’re remembered not only for their smashes “The Letter” and “Cry Like a Baby,” but as the launching pad for singer Alex Chilton, who went on to become one of rock’s most revered cult figures thanks to his groundbreaking power pop unit Big Star. In his teenage years, Chilton was an amazingly gritty Memphis soul belter akin to an American version of . . . Stevie Winwood. The Box Tops’ music also encompassed touches of pop and psychedelia, although the group’s own lack of control over it eventually led to their split. The Box Tops began life as the Devilles, a white R&B group . . . . After the band’s local popularity blossomed, teenage singer Alex Chilton joined up, and [they] quickly caught the attention of songwriters/producers Chips Moman and Dan Penn [who wrote “Sam”], who were on the lookout for a . . . Winwood-type white soul singer. . . . [T]hey signed with Bell Records . . . . The first single . . . “The Letter,” rocketed to the top of the charts in 1967, not only spending four weeks at number one but ending up as Billboard magazine’s top number one single of the year. (Chilton was all of 16 at the time.) . . . Penn began to exert more control over the group . . . frequently us[ing] session musicians . . . sometimes replacing the whole band behind Chilton . . . . “Neon Rainbow,” didn’t do nearly as well, but the Box Tops managed another massive hit in 1968 with the Dan Penn/Spooner Oldham tune “Cry Like a Baby,” which went to number two . . . . Although a couple of minor hits followed . . . Chilton was rapidly growing dissatisfied with the inconsistency of the material the[y] were handed . . . . [and] chaf[ed] at Penn’s extreme reluctance to allow him to record his own original compositions. By the time of the Box Tops’ fourth and final LP . . . Penn had bowed out . . . . [T]he Box Tops began to disintegrate. When their contract expired in February 1970, they officially disbanded, and Chilton moved to Greenwich Village for a while. . . . [He] soon returned to Memphis and joined an Anglo-pop outfit run by his friend Chris Bell[ that] morphed into Big Star, one of the most revered and mercurial bands in power pop . . . history.

https://www.allmusic.com/artist/the-box-tops-mn0000624504#biography

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