61. 'The Amateurs' (2005)
Remember that stretch in the late Nineties and early 2000s when porn was suddenly cool and mainstream? Somewhere out of that mélange came this insane, star-studded film about a small town that decides to produce an amateur skin flick. Observe! The scene where they're shocked to discover that the three black guys they've hired all have ordinary-sized penises. Behold! The scene where they convince a lovesick single woman to masturbate on camera. Watch! As Jeff Bridges tries to ask Lauren Graham to act in his porno and instead gets a date out of it. (It's only 12 years old but there's no way this movie could get made today.) As the depressed, unemployable dad at the center of this fiasco – he's the one who gets the idea, in a burst of stylized ranting and flailing – Bridges hams it up way more than usual. He's clearly trying to breathe some life into this thing. All he does is make it more bizarre.