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Rolling Stone #665 (September 1993)

Rolling Stone magazine featured the 24-year-old Janet Jackson on the cover of the September 1993 issue in a provocative topless pose, her breasts covered by her then-boyfriend’s hands. The cover caused a great deal of controversy and has since become one of the most iconic magazine covers in the world.

September 1993, incidentally, saw the debut of another world-famous cover. This other cover features Harley Quinn in her comic debut in The Batman Adventures #12.

Source: Time Magazine