Heathers was originally released in 1988, at a time when its Black Comedy, while undoubtedly edgy even then, was put at a safe distance from its teenage audiences by way of taking Refuge in Audacity. Every year since has seen that distance slowly narrow, as successive current events made it seem a lot less ridiculous.
- For one thing, there's the entire central plot of the film. When Heathers was made, the humor came from the absurdity of the idea of 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.
- To start, J.D. is eerily similar to the Columbine killers, Eric Harris and Dylan Klebold, in a number of ways. Harris filled his diary with the same kind of antisocial ranting that J.D. spouts throughout the film, and J.D.'s prediction that his actions would become a generational touchstone, the "Woodstock of The '80s", mirrors the impact that Columbine had on society, particularly with how it ignited a widespread debate over school bullying and youth depression. At the end of the film, J.D. also wears a black trench coat, rigs up the school with bombs, and kills himself, just like the Columbine killers (the only reason the bombs at Columbine High School failed to detonate was because of poor worksmanship on them. Harris and Klebold planned to kill over 250 people and top the Oklahoma City bombing, and had they done a better job wiring the timers, they likely would have gotten their wish).
- Columbine proved only to be the first high-profile case in what has become a disturbingly regular pattern of mass school shootings: a low simmer of small incidents every month in which only one or two people die or get injured, occasionally boiling over into a mass killing roughly once every year or two, whereupon there is a great public outpouring of grief but very little materially changes. In a bitter irony, the 2018 TV reboot itself was delayed because of the Marjory Stoneman Douglas High School shooting, which it would've premiered only weeks after.
- The idea of upper-middle class high school students committing mass suicide wasn't even necessarily absurd when the movie was made — in the movie's own DVD commentary, screenwriter Daniel Waters notes that Plano, Texas, a Dallas suburb notorious for being an archetypal, upper-middle class Stepford Suburbia, was once known as the suicide capital of America.
- It's worth noting as well that society has evolved greatly on mental illness and depression, particularly in teenagers, and suicides are known to (or at least feared to) trigger cascades of subsequent suicides and that a suicide is only the sad ending to a long and painful struggle that can be entirely invisible even to close friends and family. This film was actually ahead of its time in that regard, applying similar logic to a fake series of suicides when Martha Dunnstock tries to kill herself.
- Heather Chandler (Kim Walker) throws at Heather Duke (Shannen Doherty) the immortal line, "Did you have a brain tumor for breakfast?". This wound up stinging in two separate ways.
- First of all, Walker died of just that, a brain tumor, twelve 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.
- Furthermore, as of 2015, any cancer jokes thrown towards a character played by Doherty become even less amusing after she was diagnosed with breast cancer, which became stage 4 in 2020, and ended up reaching her brain in 2023.
- The character Peter Dawson (sort of a nerdy, sycophantic character on the yearbook staff) says, as voice-over, "Dear God, please don't let this happen to me, 'cause I don't think I could handle suicide," while at Heather Chandler's funeral. Jeremy Applegate, the actor who played Dawson, 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. She was even cast on the former from her work in this.
- After an outbreak of gay teen suicides in 2010 that inspired the It Gets Better Project, it can be cringe-inducing to watch the part focusing on the two heterosexual football players who supposedly killed themselves because they were gay and saw no hope of being accepted for who they were, and the townspeople's reactions. The fact that they weren't gay, and had actually been murdered, does little to lessen it.
- The student attempting to kill herself can be hard to watch due to reports of students killing themselves due to the extreme bullying they fall victim to on social media, which have become prominent ever since the mid-'00s.
- The means by which Heather Chandler is killed (having drain cleaner slipped into her "hangover cure") became this in light of the "Tide pod challenge", where teenagers filmed themselves eating pods of Tide laundry detergent — a social media stunt that Proctor & Gamble themselves, the makers of Tide (after some disbelief that it was even real), had to speak out against.
