Released as a single in March 1967, "Leopard-Skin Pill-Box Hat" peaked at number 81 on the American Billboard Hot 100 chart in June 1967.

[2][3] Frustrated with the lack of progress made with the Hawks in the New York sessions (only one song, "One of Us Must Know (Sooner or Later)", had been successfully realized), Dylan relocated to Nashville, Tennessee in February 1966, following the recommendation of his producer Bob Johnston.

[10] On April 24, 1967, an edited version lasting 2 minutes and 20 seconds was issued as a single in the United States, Canada, and the Netherlands.

[10] The single was also released, either in 1967 or around 1967, in Australia, Denmark, France, Greece, New Zealand, Norway, Portugal, South Africa, and West Germany.

[17][18] Dylan satirically crosses this accessory's high-fashion image with leopard-skin material, perceived as more downmarket and vulgar.

[19][20] In the last verse, the narrator says that he is aware that the woman has a new partner: "I saw him makin' love to you / you forgot to close the garage door".

[19][20] Some journalists and Dylan biographers have speculated that the song was inspired by Edie Sedgwick, an actress and model associated with Andy Warhol.

[22][22] Scholar of English Graley Herren wrote in 2018 that "most Dylanologists consider Sedgwick the subject of jealous mockery" in the song.

[28] another of Dylan's biographers, Robert Shelton interpreted the song as "A sustained joke about mindless excess", where "the hat could mean any trend in fashion or speech, popular or high culture".

[34] When the single was released, a Billboard reviewer considered that both sides were "powerful off-beat" numbers with "strong dance beats and compelling Dylan lyrics loaded with teen sales appeal".

[37] A staff writer for Cash Box described "Leopard-Skin Pill-Box Hat" as a "raunchy blues-type item" that Dylan's fans would find agreeable.

[38] Musicologist Wilfrid Mellers described the music as "a frisky boogie rhythm, with plangent blue notes so rapid that they sound more like chortles than sighs".

[40] "Leopard-Skin Pill-Box Hat" was dismissed as a "minor song" by Michael Gray, who thought that it was merely a "good joke and a vehicle for showing Dylan's electric lead guitar-work".

[43] A 2015 Rolling Stone listing of Dylan's best songs included "Leopard-Skin Pill-Box Hat" in 67th position, referring to it as "a little masterpiece of inside-out innuendo and twisted double-entendre".

[48] On July 7, 1984, Dylan performed the song with Clapton and Chrissie Hynde at Wembley Stadium as part of his tour with Santana.