Election (1999)

The sharpest film here about ambition, and the one that changes most when you rewatch it as an adult. Reese Witherspoon's Tracy Flick is the overprepared student running for student government president, Matthew Broderick is the civics teacher who decides to stop her, and Alexander Payne makes it painfully clear that the grown-up is the one behaving like a child. Adapted from Tom Perrotta's novel and set at a high school in Omaha, Nebraska, it earned an Oscar nomination for Best Adapted Screenplay. The comedy is cringe rather than slapstick, and it is frank about sex, so this is very much an adult's film about teenagers rather than one to share with them.