27. To Sir, with Love (1967)
Way before Mr. Holland began teaching his opus and Michelle Pfeiffer was molding dangerous minds, Sidney Poitier was taming a room of unruly British teens with his real-life lessons and tough-love tactics (a boxing glove to the stomach, anyone?). Having himself played an insubordinate kid in 1955's Blackboard Jungle, the student masterfully becomes the teacher in this sappy but never maudlin tale of inspiration and tolerance. —Michelle Kung
Image Credit: Everett Collection
50 Best High School Movies
As Emma Watson's ''Perks of Being a Wallflower'' arrives, see our honor roll of all-time great high school flicks like ''Sixteen Candles,'' ''Easy A,'' ''Say Anything,'' ''Mean Girls'' -- and our No. 1
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