October 1999Photograph By Sam Jones

In 1999, Clooney was knocking on the door of movie star-dom, he had so far been known mostly for his role on the hit TV show ER, when he teamed up with the Coen brothers on O Brother, Where Art Thou? He would go on to appear on Esquire’s cover nine times. Here in his first shoot, he poked fun at himself and at celebrity.