A Brief History of Controversial Art
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Brooke Shields Portrait, Gary Gross
Gah. Crypto-pornographer Gary Gross took this ghastly picture of Brooke Shields in 1975 for a Playboy publication called Sugar 'n Spice. Then fancy-pants Richard Prince just had to go and reproduce it for his 1981 collection, Spiritual America. It was removed from a show at the Tate Modern in 2009 after protests (about its "obscene nature" rather than its tackiness).