Election (1999)
Director: Alexander Payne
Is it strange to see this as Payne's highest entry on this list? Surely one would have expected the broader, more audience-friendly Sideways to have snagged that spot. In retrospect, perhaps not. A film that manages the gargantuan task of goosing both the Darwinian proving ground of high-school USA and the Byzantine machinations of the American political system, Election is satire masquerading as quirky comedy. A canny adaptation of a Tom Perrotta novel, it was initially inspired by the Bush-Clinton election of 1993 and the infamous case of a pregnant prom queen denied her title after staff rigged the vote. Regarding the latter, it's possible to view Election - in which teacher Matthew Broderick attempts to sabotage monstrously ambitious student Reese Witherspoon's bid for student body president - as not merely bang on target but also, in the light of the Florida 2000 fiasco, remarkably prescient. Read Review