100 Greatest Bob Dylan Songs

From "Just Like a Woman" to "John Wesley Harding," we count down the American icon's key masterpieces

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67. "Leopard-Skin Pill-Box Hat" (1966)

Not many songs about sexual jealousy are as hilarious as this loping, snarling 12-bar Chicago-style blues number. The Blonde on Blonde recording has the loose, stumbling tone of a one-take throwaway, but in fact Dylan uncharacteristically took 22 different stabs at "Leopard-Skin Pill-Box Hat" over the course of four sessions in six weeks; an earlier, slower ramble through it can be found on the No Direction Home soundtrack.
 It's a little masterpiece of inside-out innuendo and twisted double-entendre: the drunken hookup implicit in "just like a mattress balances on a bottle of wine," an invitation to see the sun rise, followed by "We'll both just sit there and stare." And who's the victim of Dylan's invective here? Rumors suggest that it's fashionable-hat-wearer Edie Sedgwick, with whom he'd been spending time not long before. When asked about the inspiration in Rolling Stone, Dylan was typically cagey, saying the song was just about a hat: "Mighta seen a picture of one in a department store window."

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