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.
Is Veronica manipulated into killing Heather Chandler and Kurt Kelly, or did she know exactly what she was doing? When she takes the cup of poison to Heather, she feels for the mug while kissing J.D. The poison mug has a lid, while the safe one does not. The film clearly shows Veronica's hand on the lid, indicating that she knew exactly which cup it was. Likewise, when she lures Kurt and Ram to the woods, J.D. shoots Ram with what J.D. has told her are tranquilizers, but are in fact real bullets. Veronica misses Kurt, who runs off, J.D. giving chase. While they are running, Veronica examines Ram's corpse, and it is clear that she knows it is really a corpse. Then when J.D. chases Kurt back, she shoots him. So, was Veronica manipulated into killing Heather and Kurt, or did she know exactly what she was doing?
J.D. even argues that Veronica knew exactly what she doing but acted horrified because she couldn't face that that was exactly what she wanted.
Did J.D. bounce around from school to school only because his father needed to do demolition jobs in different cities? Or did his father have a keen nose for when his son started trying to get his own back at the cliques in his schools? J.D. seemed awfully ready to scare the pants off the football jocks, being armed with a gun that shot blanks after a Pre Ass Kicking One Liner.
Genius Bonus: One of the earliest hints that Veronica's dream sequence is a dream is the reference to Eskimos in Antarctica, whereas they're actually found in the Arctic.
The word does appear in Moby-Dick, just not with that spelling. (excerpt) The fact is, that among his hunters at least, the whale would by all hands be considered a noble dish, were there not so much of him; but when you come to sit down before a meat-pie nearly one hundred feet long, it takes away your appetite. Only the most unprejudiced of men like Stubb, nowadays partake of cooked whales; but the Esquimaux are not so fastidious. We all know how they live upon whales, and have rare old vintages of prime old train oil. Zogranda, one of their most famous doctors, recommends strips of blubber for infants, as being exceedingly juicy and nourishing. And this reminds me that certain Englishmen, who long ago were accidentally left in Greenland by a whaling vessel- that these men actually lived for several months on the mouldy scraps of whales which had been left ashore after trying out the blubber. Among the Dutch whalemen these scraps are called “fritters”; which, indeed, they greatly resemble, being brown and crisp, and smelling something like old Amsterdam housewives’ dough-nuts or oly-cooks, when fresh. They have such an eatable look that the most self-denying stranger can hardly keep his hands off.
Harsher in Hindsight: It seems as though, every year, something happens that makes the film just that much more uncomfortable to watch.
For one thing, there's the entire damn movie. When Heathers 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 sucked the darkly hilarious fun right out of the movie. The fact that Eric Harris specifically rigged up his school with bombs and filled his diary with the same anti-society ranting that J.D. spouts only makes it worse.
Both the Columbine killers wore dark trench coats eerily similar to what J.D. wore in the final scene.
The idea of white, upper-middle class high school students committing mass suicide wasn't even necessarily absurd when the movie was made - as noted in the movie's own DVD commentary, the scriptwriter notes that Plano, Texas (a community almost notorious for being almost exclusively made up of white, upper-middle class residents) was once known as the suicide capital of America.
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.
The character Peter Dawson prays he will never commit suicide. His actor, Jeremy Applegate, committed suicide on March 23, 2000.
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, Beverly Hills 90210 and Charmed, due to her poor relations with her fellow cast members.
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 mineral water in the jocks' bags as evidence that they were gay. These days, drinking mineral water isn't considered sissy or snobby; at worst one might be thought of as slightly over-health-concerned. 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.
Actor Shipping: Barret Wilbert Weed and Ryan McCartan, the original Veronica and J.D., get this a lot. Weirdly, Ryan's successor, Dave Thomas Brown, seems to get left out of it, even though Ryan's been dating Dove Cameron for a while now.
There are two types of J.D. fans: those who see him as the tragic, complex, and likable, but ultimately villainous, obsessive, and murderous character he is, and those who see him as a misunderstood Woobie whose behavior towards Veronica is romantic. The former tend to find the latter incredibly embarrassing. (Luckily, they're a Vocal Minority.)
Similarly, there are those who ship J.D. and Veronica, but realize and admit it's an unhealthy trainwreck and would never want anyone to be in a relationship like that in real life (as one fan put it, "No one hates J.D./Veronica shippers more than we hate ourselves."), and those who think they're a perfect couple who are tragically beautiful together. Again, the former don't get along with the latter.
Ear Worm: Most of the songs in the musical, especially "Dead Girl Walking", "Candy Store," "Meant to Be Yours", "Beautiful", and "Blue."
"Who-o-o-o-oah!" "C'mon, Westerburg!"
"Full steam ahead, take this dead girl walking! Let's break the bed, rock this dead girl walking!"
"Freeze your brain, swim in the ice, get lost in the pain! Shut your eyes tight, 'til you vanish from sight, let nothing remain!"
"Box up my clothing for Goodwill, and give the poor my Nordic Track. Donate my car to crippled kids, or to those ghetto moms on crack..."
Heather Duke crosses it in "Shine a Light (Reprise)" by mocking Heather McNamara's attempt at suicide and saying she deserves to die for "whining." J.D. appears to agree, seeing as how he starts plotting to kill her after she does that.
The fandom's split on whether or not J.D. ever crossed it, and if he managed to redeem himself by sacrificing himself to save Veronica. However, for fans that think J.D. crossed it, him plotting to blow up the school is generally where they say he did.
Most Wonderful Sound: Barret Wilbert Weed!Veronica's laugh, which is adorably awkward. It helps that it's so infectious.
Narm Charm: Many songs run on this. For example, "Seventeen" is about mundane things like watching bad movies and eating chili fries. "Kindergarten Boyfriend" is Exactly What It Says on the Tin. They should be hard to take seriously, but due to beautiful music and sincere acting, they're both genuine tear jerkers.
Painful Rhyme: "My problems were myriad—" "I was having my period." (An intentional example, if Veronica's awkward laughter and J.D.'s "uhhhh" expression afterwards are anything to go by.)