The Coen brothers are celebrated for their quirky, ambiguous, and thought-provoking movies, and they are at their most creative when working with George Clooney. Joel and Ethan Coen have been making movies since 1984, and though their output together has slowed down, they have built a Rolodex of regular A-list collaborators. One of those collaborators is movie star George Clooney, who first worked with the filmmaking brothers on the over-the-top musical comedy O Brother, Where Art Thou? That movie was a modest success at the box office and a critical hit, and since then, the filmmakers and actor have worked on four more outrageous movies together.

Clooney is best known as the charming, stable, and reliable protagonist, whether it's in something as ridiculous as the Clooney-hated Batman and Robin or as thrilling as Ocean's Eleven. The actor has built his career on his charisma, but that's what makes his collaborations with the Coen brothers so fascinating.