- Fargo: The Coen brothers lead off this list with hopefully the only comedy ever written that includes an agreed-upon-by-most-to-be-funny scene involving a man jamming another man's leg into a wood chipper with a block of wood. In the Coens' world, that's just what happens when scoundrels try to pull the strings of lunatics. Human folly, irony, being pulled into the grave by one's own nit-witted caper: these are the earmarks of one of the 90's finest examples of black comedy.
- American Psycho: Either the book or the movie. Which is more evilly hilarious: the scene in which nascent serial killer Patrick Batemen drools over a rival's perfect business card, or the scene in which he lays out a critique of the career of Huey Lewis before splitting that same rival's skull with an ax? Bateman is a relentlessly funny send-up of 1980s materialistic narcissism. Also, he wants to play with your blood.
- To Die For: Me Culture is again the target in the movie that arguably defines Nicole Kidman's career. In it, she played a dogged social climber of a TV journalist who hired three lusting boys to kill her husband. Kidman's Suzanne Stone didn't need talent to secure the spotlight, she just needed an undeviated focus toward that goal. This movie is greater than the sum of its parts: it's not that hilarious, and it doesn't cut that deeply, but it's profoundly disturbing and will have you thinking about how you almost laughed (but were too put off) for days.
Society Has Problems
- Storytelling: Most people hate this movie. In these two short films that combine into a satisfying whole, filmmaker Todd Solondz allows his characters to speak honestly for themselves, and in so doing they reveal their faults and failings so plainly that -- although you laugh at them -- you cannot help but be touched by the sorrow they receive alongside their respective educations, and the ferocity with which it's delivered. As a side note, anybody who's ever taken a creative writing workshop in college can vouch for how accurate the related scenes are.
- Vernon God Little: Winner of the 2003 Man Booker Prize for fiction, this novel tells the tale of a young teenage boy from Texas who runs from the law after being falsely accused of participating in a school shooting. The news media, and by extension the public fascination with it, is the primary target -- though it isn't the only one -- in this far-reaching epic farce. I'd say everyone should read this book, but there are too many people who should be, I believe, banned from it as a punishment.
- In the Company of Men: Everyone has that one friend, or everyone knows at least one person, who is a complete asshole. This person is able to talk his way into the exploitation of anything/one. This is a movie about allowing yourself to be swept up into the majesty of assholedom. It is filled with funny-but-painful moments of cruelty, and leaves you with a simple enough message: if you fuck with assholes, you will end up covered in shit.
- A Modest Proposal: Best black humor ever? In Jonathan Swift's perfect satirical essay, he argued that the solution for the Irish overpopulation problem was to feed Irish babies to the wealthy as a delicacy, even going as far as including detailed instructions on several of the methods which could be employed to that end. Swift's satire was convincing enough that he received numerous letters from colleagues chastising him for his inhumane position. Oh, by the way: this was written in 1729.
- Brazil: Set in a future socialist Britain in which serpentine bureaucracies and fear tactics have combined to subvert the average will to live, Terry Gilliam's masterpiece even includes a role for Robert DeNiro as a rogue HVAC repairman. Of course, be sure not to miss the saddest happy ending ever captured on film.
- The Trial: An underrated Orson Welles classic based on the novel by Franz Kafka, The Trial tells the tale of Josef K's (Anthony Perkins of Psycho) quest to clear his name after he's falsely accused of an unnamed crime. Josef's irretrievable entanglement in the legal system seems to be the logical progenitor to the later Brazil, and his inability to get a straight answer from anyone is as reminiscent of Catch-22 as it is of Who's on First. It also happens to be visually dazzling.
- Delikatesy (Delicatessen): Set in a desolate future that looks like a desolate past, Delikatesy was somewhat confusingly brought to us by the same director who brought us Alien: Resurrection and Amelie. You'll have to trust that this move is nothing like those two. It centers around an apartment building run by a murderous butcher who serves human remains to sustain his tenants. The main character of the story is an out-of-work clown. Nothing further is necessary; you'll see it for yourself.
- Transmetropolitan: The only comic book to make the list -- though certainly not the only deserving one -- Warren Ellis's quasi-cyberpunk take on gonzo journalist Hunter S. Thompson is probably what a movie called The Day After Tomorrow should have really been about. Corrupt Presidents and rampant drug use abound in the only comic wherein the journalist is actually the hero rather than just the alter-ego.
Catch-22: For those that don't know, yes, this is the book upon which the saying is based. In the book, the Catch-22 is the fact that you can't leave the war unless you're crazy, but admitting that you're crazy and should leave the war proves that you're sane. Of course, the novel is nearly a cover-to-cover list of these examples of dark absurdity. War will never again be so calmly eviscerated.
- Dr. Strangelove, or: How I Learned to Stop Worrying and Love the Bomb: Ultimately, there is nothing funnier than the fact that we all inexplicably want to kill each other. We're not so different, after all. We all have War Rooms. We all have mine shafts. We all have the Bomb. Ah yes, the atomic bomb: one of man's greatest theoretical achievements harnessed for the purpose of... uh... blowing shit up. Additionally, Peter Sellers is brilliant times three.
Outright Confronting Death
- Harold and Maude: For years, I avoided seeing this movie because I didn't want to see a love story between a teenager and an old woman. The fact is, I still don't, but in spite of that, this movie is well worth the punishment. Harold's obsession with death plays well with his March-December romance, and you'll probably be hooked -- as I was -- by the running gag of his faked suicides. Faked suicides aren't funny, you say? I'll fight you.
- Waiting for Godot: You can interpret Beckett's masterpiece as anything from pompous and glib to genius and profoundly existential. If you haven't seen or read it, be aware that it and you have been around too long for you not to have seen or read it. It raises unavoidable questions, though. Namely: what is this game we're playing? And what the fuck are we waiting for?
- Arsenic and Old Lace: Frank Capra's 1944 masterpiece fails to make the list because I neither appreciated nor expected the extreme hamminess of the acting.
- Fear and Loathing in Las Vegas: I just didn't see a place for reality-bending "non-fiction," and besides, while Fear and Loathing is amazing, it's comparatively not that dark.
- Art School Confidential: Overlooked little gem with an unsettling tonal shift that drives viewers nuts. Especially keep an eye out for Jim Broadbent's phenomenal turn as a psychotic older artist.