3. Lip-Syncing Transvestite - The Harvest (1992)
Actors have to do terrible things in the name of making a living for themselves, and that material invariably gets traded around the internet once the talent makes it big and moves away from playing such roles. Such is the case with Clooney's "performance" in the little-seen, but now infamous The Harvest, in which he was given the auspicious cast billing of "Lip-Syncing Transvestite," a role which probably now haunts him given how many hits its got on the net. In a throwaway scene - which explains the character name - Clooney, sporting a glorious blonde shock wig and golden padded underwear under his leather jacket, swings chimpanzee-like towards the camera, clearing under instruction to sing along seductively. Ignoring the ignominy of the role, it's the artistry of the performance that's a real issue here: Clooney clearly had one job, and he fails it miserably. Not only is he the least convincing transvestite in the history of transvestism, his attempt at seduction has completely the opposite effect as presumably intended.