1. Lord Love A Duck (1966)
In his directorial debut, underrated satirist George Axelrod takes shots at seemingly every American institution from the church to show business, but he saves his most potent vitriol for the ruthless high-school caste system. Just a few years away from playing a high-school teacher in Pretty Maids All In A Row, a suspiciously middle-aged Roddy McDowall stars as a brilliant, mysterious high-schooler who serves as a psychotic fairy godfather of sorts for deeply troubled teen queen Tuesday Weld. The twisted relationship between the heartbreakingly gorgeous Weld and the mysterious loner McDowall eerily anticipates both the central dynamic in Heathers and Weld's equally deranged affair with Anthony Perkins in the simpatico 1968 black comedy Pretty Poison.
2. If… (1968)
A benchmark in counterculture filmmaking, Lindsay Anderson's portrait of a revolt staged at a British boys' school converts the abuses heaped on school kids into a clanking metaphor for the repression of British society in general. A thousand years of tradition goes up in smoke as rebellious senior Malcolm McDowell turns on the "whips," a group of fascist students who uphold the school's draconian rules by caning those who break them. After coming upon a cache of weapons, McDowell and his buddies, referring to themselves as "The Crusaders," start taking out authority figures from the rooftops, sparking a full-scale rebellion. It's like the climax to Jean Vigo's classic 1933 film Zero For Conduct, only with bullets instead of pillow feathers.
3. Pretty Maids All In A Row (1971)
In Roger Vadim's deliciously warped black comedy, a seldom-better Rock Hudson plays a jovial high-school coach/faculty advisor so beloved that not even his unfortunate predilection for murdering fetching female students can dim his popularity. Star Trek creator Gene Roddenberry produced and scripted this cheerfully misogynistic adaptation of Francis Pollini's darkly comic novel. The Osmonds, of all people, provided the theme song. Legendary libertine Vadim refuses to cast judgment on the sexual shenanigans of a hormone-crazed Southern California high school so debauched and surreal that it all but qualifies as an alternate universe. It's one of cinema's few ambiguous, almost-positive portrayals of serial killing.
4. Pink Floyd: The Wall (1982)
As part of his perverse quest to create the most visually and aurally oppressive movie possible, director Alan Parker stocked his feature-length music video with unrelentingly grim images of life under totalitarian rule. Granted, there's really no way to find a sunny interpretation of Pink Floyd's "Another Brick In The Wall Part 2," with its lobotomized chorus of children chanting, "We don't need no education. We don't need no thought control." But Parker goes further than depicting "dark sarcasm in the classroom"; his conformist kids are lined up on a factory belt and fed through a meat grinder, where their innards are presumably processed for neo-Nazi cookouts.
5. The Breakfast Club (1985)
The key element in John Hughes' sinister plot to control the minds of impressionable, self-absorbed teenagers across America, The Breakfast Club offers a collection of high-school stereotypes so broad—The Jock, The Geek, The Princess, The Judd Nelson, etc.—that everyone can identify with at least one of them. Gathered in the world's most luxurious public-school library for Saturday detention, they each confess (some sooner, some later) that teenage life isn't all it's cracked up to be. Even the Jock (Emilio Estevez) and the Princess (Molly Ringwald), the symbolic King and Queen of the school, tearfully admit that the pressure of being on top outflanks the benefits. And as in all Hughes movies, the authority figure (Paul Gleason) is a contemptible boob.
6. Lean On Me (1989)
The story of Joe Clark, a New Jersey inner-city principal who saved a school from getting shut down by the state, is supposed to be inspiring; it's directed by John G. Avildsen, who made Rocky and The Karate Kid, and it stars Morgan Freeman, a presence of great warmth and quiet authority. Yet who takes inspirations from a bat-wielding thug who goes to Machiavellian extremes just to achieve higher test scores? The real Clark went on to work at a juvenile detention center; it probably wasn't much of an adjustment for him.
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