Playboy has always been a purveyor of the social climate, a cultural and sexual innovator that happens to have an exceptionally good eye for beautiful women. With that in mind, Playboy writer Damon Brown, with the help of Hugh Hefner, looked back over the history of the magazine to come up with the greatest covers that graced newsstands.

From the 1953 Marilyn Monroe cover that started it all to Darine Stern as one of the first African-American women to appear on an American cover, Playboy’s Greatest Covers balances the world’s most exciting women with the story behind it all.

Today we’re giving away four copies of the hardcover book. To enter, just tweet your favorite cover to @Playboy with the hashtag #GreatestCovers.

Check out more of our favorite covers on Facebook.

(Top left: October 1971, Darine Stern; March 1980, Bo Derek, one of the first women as a repeat Playboy cover model)

Read the full sweepstakes rules and regulations.