These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
More straddling the line between this and Fridge Logic, but - Rob is a 23-year-old pretending to be a high-school student, who plays baseball. Most, if not all, governing bodies would force South Glen South to forfeit the games in which he played, as players over 18 are a big no-no a high school sports.
Hilariousin Hindsight: Seeing James Franco as one of the popular jerks and Leelee Sobieski as a bully-target becomes almost karmic when you see the ending to The Wicker Man remake.
Leelee Sobieski as the nerdy girl, especially when she strips down to that spandex blue cat suit at the prom.
Also Josie Geller — she's supposed to be a bookish, nerdy girl as well... but she's Drew frikkin' Barrymore! That said, they do manage to make Drew look pretty bad in her prom flashback. More than the majority of these examples, anyway.
Tearjerker: Josie's flashback to the night of her prom. Her younger self giddily rushes to her front porch to meet her date... only for him and his real date to cruelly pelt her with eggs and drive off, leaving young Josie sobbing.