Charles Foster Kane, Citizen Kane (1941): The unwritten rule is: likable lead chracters. They can be a bit dickish, but the audience must feel safe rooting for their betterment. In addition to being innovative in every other department, Orson Welles’ film debut also introduced Hollywood to the concept of a character who is thoroughly unlikable. Yes, he’s crying on the inside, but he sabotages every chance of happiness for himself and those around him.
Robert Cole, Modern Romance (1981): Albert Brooks’ films reveal the dark side of the Woody Allen persona, depicting neurotics not as adorable quip-flingers but the egomaniacal need-monsters they tend to be in real life. In the hilariously unpleasant film, his Hollywood editor whimsically breaks up with his girlfriend, stalks her, inexplicably wins her back, then thinks she’s cheating on him. In the film’s most infamous scene, he goes on a date post-break-up. As they get in the car, a sad song hits the radio. Verclempt, he circles the block and drops her back home, expecting that she’ll understand.
Melvin Udall, As Good As It Gets (1997): As the rumor goes, Jack Nicholson’s bestselling author—an all- purpose bigot and temperamental egomaniac—was so despicable writer- director James L. Brooks decided at the last minute to make him suffer from OCD, opportunistically hoping the disorder would make him cute and less responsible for his toxic horridness. Pussy.
Roger Greenberg, Greenberg (2010): Ben Stiller’s 40ish wastrel may have just emerged from a mental hospital, but even that can’t soften a character so cruel, odious and heartless a fellow critic has taken to renaming the film simply Asshole.
In Kicking and Screaming —the 1995 indie, not the Will Ferrell soccer comedy—writer-director Noah Baumbach presents a group of aggressively quotable and painfully self-conscious malcontents so afraid to leave their comfort zone they spend a full year in their college town post-graduation. If they stayed on the same path, if they didn’t progress emotionally, vocationally or even verbally, it’s likely they would curdle into Roger Greenberg (Ben Stiller), the caustic, egomaniacal, acid-tongued fuckhead at the center of Baumbach’s sixth feature. Like Kicking and Screaming, Greenberg is a quote machine. When asked how he’s doing, Roger quips, “Leonard Maltin would give me two and a half stars”—just as...
Another great Italian neo-realist weepie from Vittorio De Sica—who had already given the world Shoe-Shine and Bicycle Thieves —this tale finds an old genetleman (Carlo Battisti) so impoverished he seeks to off himself.
Neil Barsky’s "Koch" Keeps It Light