Actors’ behind-the-camera debuts are rarely great. There’s generally a safeness to those movies, where it feels more like an actor testing the waters than having a story they need to tell. A big exception to that trend: George Clooney. Clooney took a major chance on Confessions of a Dangerous Mind. Sure, he had a script written by Charlie Kaufman (Adaptation), but he made bold choices as a filmmaker. From the film’s complex style, the timeline they have to show in two hours, and the tonally tricky humor, Clooney’s first directorial outing was an ambitious introduction. Since then he’s tried his hand at varying material, constantly pushing himself as a filmmaker. Nothing against his films since 2002, including the overlooked Leatherheads, but Confessions of a Dangerous Mind remains his best picture. This is a film where big choices were made, and every single one of them hit their mark. It’s an emotional dark comedy that not many filmmakers could pull off.