Dr. Strangelove
When you think of nuclear war and potential annihilation of the planet, you would think the subject would exclusively be dealt with gravity, right? Not if you’re Stanley Kubrick, who deftly skewers the Cold War with a biting satirical edge. Peter Sellers is amazing in multiple roles, including the former Nazi title character and the President of the United States, whilst the decision to have George C. Scott play his role as a jingoistic general completely straight, pays off in spades. Throw in dark tensions about an impending war between the US and the USSR, classic lines (“You can’t fight here, this is the War Room!”) and classic imagery (Slim Pickens riding a nuclear bomb), and you have a contender for Kubrick’s best film.

The Big Lebowski
The Coen Brothers are masters of dark comedy, and Lebowski demonstrates their aptitude. A neo-noir parody, we follow The Dude, the ultimate slacker, as he gets caught up in a curious adventure concerning the disappearance of the daughter of a wealthy socialite who shares the same name as him. Featuring John Goodman as crazed Vietnam veteran Walter, bowling being taken ridiculously seriously (to the point where guns are drawn), White Russians, ear biting, and John Turturro as a Latino pederast bowler named Jesus, this may be the most bizarre film in the Coen’s oeuvre, and it’s all the better for it.

Team America: World Police
Satirising the War on Terror, overly political celebrities and Jerry Bruckheimer action movies, the creators of South Park bring their usual dark wit and cynicism to a movie involving puppets. Like in South Park, this film crosses the line multiple times with great hilarity, featuring graphic puppet sex scenes, musical numbers about everybody having AIDS, Other notable features include the fervent patriotism of America, a highly effeminate Kim-Jong Il as the villain, and hilarious caricatures of everyone and everything, particularly politicians. Also, Matt Damon.

In Bruges
This film about two hired assassins botching their job and hiding out in Bruges is ripe for black comedy, with Martin McDonagh delivering a deep and hilarious character study. One of the most wonderfully profane movies ever, it features some of the greatest explicit insults of all time. Colin Farrell brings a deep and moving portrayal to his character, conflicted about his career as an assassin, whilst also being rude towards dwarves, in some wonderfully crossing-the-line humour. It’s tragic, shocking and hilarious, and brings a new perspective to the violent comedy genre.