Esquire‘s Blast from the Past

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Esquire‘s May 2008 cover, featuring Fabrizio Ferri‘s photograph of Jessica Simpson in mid-shave, is an homage to designer George Lois‘s March 1965 cover of Italian actress Virna Lisi similarly engaged, coiffed, and thickly eyelinered. (Look closely and you’ll note that both blondes wield a Gillette Superspeed razor, although Simpson’s vintage model had to be tracked down on eBay.) It’s Esquire‘s second iconic cover recreation as part of its 75th anniversary celebration (the first, in February, involved a quartet of be-turtlenecked Victoria’s Secret models).

The magazine’s May issue devotes a page to the backstory, including Lois’ inspiration for the original cover: an article entitled “The Masculinization of the American Women,” which Esquire‘s present-day editors advise you not to bother reading. “I wanted to capture a woman being manly and still beautiful,” says Lois. “It was a spoof of the whole idea of a glamorous Hollywood.” Marilyn Monroe, Jayne Mansfield, and Kim Novak refused to participate before Lisi (who appeared with Jack Lemmon in the 1965 film How to Murder Your Wife) jumped at the chance. And Monroe and co. weren’t the only hard sell. “The ad guys hated it,” says Lois of the cover. “It was too edgy.” Razor pun intended, we hope.