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"Leopard Skin Pill Box Hat" is a song by American singer songwriter Bob Dylan, which was released on the second side of his seventh studio album Blonde on Blonde (1966). The song was written by Dylan, and produced by Bob Johnston. Dylan has denied that the song references any specific individual, although critics have speculated that it refers to Edie Sedgwick, who Dylan had spent time with in December 1965. After several takes on January 25 and 27, 1966, in New York, the final version was finally achieved in the early hours of March 10 in Nashville. 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. Critics have not rated the song amongst Dylan's best, although the song's humor has been praised. From 1966 to 2013, Dylan played the song live in concert over 500 times.

The song was one of the first compositions attempted by Dylan and the Hawks when in January 1966 they went into Columbia recording studios in New York City to record material for Dylan's seventh studio album, which was eventually released as the double album Blonde on Blonde. Two takes of the song were attempted on January 25, and four takes on January 27, but none of the recordings were deemed satisfactory. 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. Johnston hired experienced session musicians, who were joined by Robbie Robertson of the Hawks, and Al Kooper, who had both played at the New York sessions. Dylan completed the lyrics for the song between the New York and Nashville sessions. In Nashville, the evening of the first day of recording, February 14, was devoted to "Leopard Skin Pill Box Hat". Present at the session were Charlie McCoy (guitar and bass), Kenny Buttrey (drums), Wayne Moss (guitar), Joe South (guitar and bass), Kooper (organ), Hargus Robbins (piano) and Jerry Kennedy (guitar). Earlier in the day Dylan and the band had achieved satisfactory takes of "Fourth Time Around" and "Visions of Johanna" (which were included on the album), but none of the 13 takes of "Leopard Skin Pill Box Hat" recorded on February 14 were to Dylan's satisfaction. Dylan soon left Nashville to play some concerts with the Hawks. He returned in March for a second set of sessions. A satisfactory take of "Leopard Skin Pill Box Hat" was finally achieved in the early hours of March 10, 1966. Dylan sang on the track, and played electric guitar and harmonica. Kennedy was absent, but, in addition to the musicians from the earlier session, Henry Strzelecki was on bass, and Robertson was on lead guitar, though Dylan himself plays lead guitar on the song's opening 12 bars.

Blonde on Blonde, Dylan's seventh studio album, was issued as a double album on June 20, with "Leopard Skin Pill Box Hat" as the third track on side two. The album version had a duration of three minutes and fifty eight seconds. The song was included on an EP in West Germany in late 1966. 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. The first take from January 25 was released on The Bootleg Series Vol. 7: No Direction Home: The Soundtrack (2005). The recording sessions were released in their entirety on the 18 disc Collector's Edition of The Bootleg Series Vol. 12: The Cutting Edge 1965–1966 (2015) with highlights from the February 14, 1966, outtakes appearing on the 6 disc and 2 disc versions of that album.

"Leopard Skin Pill Box Hat" is a 12 bar blues,; melodically and lyrically it resembles Lightnin' Hopkins's "Automobile Blues", English language scholar Douglas Mark Ponton wrote that although Dylan has sometimes uses Delta blues themes such as love, sex, mourning and anxiety when composing original blues songs, "he also brings his own kind of lyrical inventiveness to the form, taking it into new semantic territory." Ponton takes "Leopard Skin Pill Box Hat" as an example, where Dylan takes a piece of clothing that is outside the traditional blues lexicon into his song, rather than using the metaphor of an automobile for a woman that had been used by Robert Johnson and Hopkins. Another possible influence, identified by Craig McGregor in The Sydney Morning Herald, is "In the Evenin'". 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". 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. 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". He felt that Dylan "defuses negative emotions with humour" in the song. Conversely, music critic Paul Williams felt that it was "the only really mean spirited song on the album". "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". However, Gray did acclaim Dylan's delivery of "You know it balances on your head / Just like a mattress balances / On a bottle of wine", arguing that "it would be hard to find a better instance of words, tune and delivery working so entirely together". Author John Nogowski rated the song as "B+", and described it as a "standard blues, with some funny lyrics". He noted that the track is the only one that credits a guitar solo to Dylan, but felt "He's no Eric Clapton, but it's fun, nevertheless." Neil Spencer gave the song a rating of 4/5 stars in an Uncut magazine Dylan supplement in 2015. 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". The same year, USA Today ranked 359 of Dylan's songs, placing the track at number 200. Jim Beviglia had rated it 166th amongst Dylan's songs in his 2013 book.

According to his website, Dylan played "Leopard Skin Pill Box Hat" 535 times in concert from 1966 to 2013. The site lists the earliest live performance as February 26, 1966, but the first known live performance was on February 5. On July 7, 1984, Dylan performed the song with Clapton and Chrissie Hynde at Wembley Stadium as part of his tour with Santana. efn|Bono rejoined Dylan for the next song in the set, Dylan's "Blowin' in the Wind", and sang his own version of the lyrics for two verses; Dylan followed the first of these with his own lyrics. Jack Whatley of Far Out described it as a "car crash duet". Cat Power has covered the song as part of her Cat Power Sings Dylan show, including a performance at the Royal Albert Hall in November 2022 in which she recreated the "Royal Albert Hall" concert. In 2013, experimental hip hop band Death Grips released a song entitled "You Might Think He Loves You for Your Money but I Know What He Really Loves You for It’s Your Brand New Leopard Skin Pillbox Hat". The song takes its title from a lyric in "Leopard Skin Pill Box Hat", although no reference to Dylan's song itself is made within their song.