26. Pretty in Pink (1986)
Perhaps the most controversial ending to a teen romance ever. (Behind Romeo and Juliet? Fine.) Should Andie (Molly Ringwald) have chased after rich, repentant Blane (Andrew McCarthy), or stayed at the prom with poor, devoted Duckie (Jon Cryer)? That we, women now in our 30s, still care is a testament to John Hughes' script about love across class lines (point for Blane); the meaning of friendship and individuality (point for Duckie); and the evil nature of wealthy high schoolers in crisp, white clothing (point for James Spader). Mandi Bierly