10 Incredibly Dark Comedies That Dare You To Laugh

7. Heathers (1988)

Despite having joined the three Heathers (played by Shannen Doherty, Kim Walker and Lisanne Falk) as the most powerful clique at Westerberg High School,Veronica (Winona Ryder) cannot stand their snobbish self-importance and so, with the help of boyfriend J.D ( Christian Slater), plans to murder them and disguise the deaths as suicide. Things quickly get out of hand, however, when this leads to a spate of copycat suicide attempts throughout the school. Realising that they have gone a step too far, Veronica breaks up with J.D - who takes his revenge by first attempting to kill her before rigging the school boiler room with explosives. By now it's too late to question just where, if anywhere, director Michael Lehmann plans to draw the line. Darkest Comedy Moment: After shooting jocks Kurt and Ram, Veronica and J.D plant a note along with 'gay materials' (a photo of Joan Crawford and, erm, a bottle of mineral water) beside their bodies to suggest they were victims of a suicide pact. At Kurt's funeral, his father proudly announces ''My son's a homosexual. I love my dead gay son''. Admittedly, this has become a different sort of awkward over the last twenty-five years...