In spite of President Ronald Reagan’s crusade against Playboy, the magazine produced some of its most iconic photography, interviews and unforgettable covers. From loud makeup to really, really big hair, 80s Playboy covers represented every aspect of the era in style, politics and entertainment. It also was a sign of new beginnings — Playboy had its last stapled magazine produced in September 1985, featuring 80s icon Madonna. These celebrity appearances began to signal a new characteristic of covers for the magazine industry as a whole, and Playboy covers certainly reflected this shift. From Steve Martin, Goldie Hawn, La Toya Jackson to Bo Derek, Playboy featured some of the decade’s most interesting and controversial subjects on its covers.