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Genius Bonus: one of the earliest hints that Veronica's dream sequence is a dream is the repetition of the word 'eskimo'. Despite what everyone says in the dream, the word appears nowhere in Moby Dick (and for that matter, Eskimos are found in the Arctic, not the Antarctic).
Kimberly Walker (Heather Chandler) utters the immortal line, "Did you have a brain tumor for breakfast?". Tragically, Walker herself died of just that, 12 years later at the age of only 32. What makes it doubly uncomfortable are the scenes with Heather Chandler's death and funeral and, later, the appearance of her ghost in a dream sequence.
Also, the character Peter Dawson prays he will never commit suicide. His actor, Jeremy Applegate, committed suicide on March 23, 2000.
Possibly the whole movie. When the movie was made, the humor came from the absurdity of the idea of white, upper-middle class high school students killing each other. Then, the Columbine school shooting happened and that sucked the darkly hilarious fun right out of the movie. If you can stand to watch it despite this, fine. Otherwise, have fun cringing.
Especially since Eric Harris specifically rigged up his school with bombs and filled his diary with the same anti-society ranting that JD spouts.
The plotline about Heather Duke being the new Alpha Bitch can be like this due to the fact that Shannen Doherty was fired from two high profile series due to being cruel to castmates.
Nightmare Fuel: J.D., of course, but his dad has a surprising amount of this considering his limited screentime. The implication that he drove J.D.'s mother to suicide probably doesn't hurt.
It's hard to imagine a film about teens actually murdering each other and planning to murder an entire school getting greenlit as a comedy these days (see the Harsher in Hindsight entry above).
One scene showed that them placing bottled water in the jocks' bags as evidence that they were gay. These days drinking bottled water isn't considered sissy or snobby so much as just normal. This is discussed in the movie, where it's pointed out that even back then, drinking bottled water was being seen as acceptable, but J.D. points out they're all the way out in the sticks where it still hasn't caught on.
Vindicated by Cable: The film, while not a box office success, found a lot of its fandom with repeated airings on WGN and TBS.
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