The 50 Greatest Esquire Covers of All Time

For Esquire's 1,000th issue, October 2015 (on sale now), we look back on the history of the magazine and launch a digital archive of everything we've ever published, Esquire Classic.

The history of Esquire—and by extension the history of this thing we call America through the magazine's lens—is told at least in part by its covers. Those images dating back to 1933, with the bylines of Ernest Hemingway and Dashiell Hammett. And to 1968, with the famous photo of Muhammad Ali. And to George Clooney in 1999 and President Obama in 2013. These are the covers that stand out above the rest, that remind us of a place in time, and the magazine that was there to capture it as only Esquire can.