Election is a favorite of mine. It's not the best movie ever made- it's not a classic of Western cinema or anything- but it's a great, biting satire rife with irony, tragedy and some great laughs.
The story focuses on a high school race for student body president; junior Tracy Flick is an ambitious, prickly overachiever who sees the race as the crowning glory of her illustrious high school career. The always-wonderful Reese Witherspoon portrays her with maniacal glee. Her opponent isn't really the football bonehead running against her in the race- it's Mr. McAllister (Matthew Broderick), a smug history teacher who blames Tracy for a scandal that ruined the career of his best friend. Mr. McAllister recruits the jock (a cute and clueless Chris Klein) and tries to rig the race.
Election is one of those rainy-day favorites I return to at least once a year. Director Alexander Payne wrote the screenplay from Tom Perrotta's novel, which I plan to read soon. I don't know how I've gone this long without reading the novel; I really enjoyed Perrotta's more recent Little Children (and its movie adaptation as well) and I'm pretty sure I'm going to love Election the novel as much as I love the movie. It's the kind of movie that gets called "quirky"- definitely not 100% mainstream fare- but if you like a good harsh satire and/or any of the lead actors, you really need to spend a rainy day with Election.