Election (1999)

If you told me that there was a really good movie starring Matthew Broderick, Reese Witherspoon, and Chris Klein, I would probably say something condescending and then not watch the movie. But in the dark comedy Election we see these actors at their best, Matthew Broderick as a spineless and powerless teacher who takes out his anger at the world on a high school student running for class president, Reese Witherspoon as an ambitious high school student intent on succeeding regardless of the consequences, and Chris Klein as a kind-hearted idiot who is coaxed into using his popularity to his advantage in public election. Sometimes election films get heavy-handed, and Election certainly could have considering its proximity to the Bush/Gore election that turned into such a debacle, but this one is simply critical without being overly referential. Election is one of my favorite dark comedies of all time. It's kind of timeless.