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25. Election (1999)
Key players: Reese Witherspoon, Matthew Broderick, Alexander Payne, Jim Taylor, Tom Perrotta, Chris Klein, Jessica Campbell
Why it's great: Satires rarely come any sharper than this. A student body election leads to a showdown between an annoyingly ambitious student (Reese Witherspoon as the indomitable Tracy Flick) and her unfulfilled civics teacher (Matthew Broderick at his recent schlubby best) who believes he can bring fairness to the race by encouraging a dimwitted but popular jock (Chris Klein) to take on the more qualified candidate. Alexander Payne's movie is precisely crafted and brimming with malicious wit. It also opened just one year before man of the people George W. Bush was elected President in a race that boiled down to a few suspiciously handled votes. That's the kind of ridiculous coincidence that transforms the high school politics of "Election" from merely hilarious to downright creepy.
- Geoff Berkshire