Say Anything… (1989)

If you've never had the urge to hold a boombox over your head outside someone's window, you probably haven't seen Say Anything… And in the realm of 'Greatest High School Movies of the 80s of All Time,' this gem is like that one kid who's cool without even trying. Fans are still split whether it's Lloyd’s trench coat or Diane’s pen that's the real MVP. Trying to debate its rank? Good luck, because not loving John Cusack here is almost a personality flaw at this point.