10. The Royal Tenenbaums
A very strange dark comedy about suicide, family, incest, and cancer. It's Wes Anderson's best film (followed quickly by Moonrise Kingdom) and an excellent depiction of perhaps the most dysfunctional family in the history of cinema. Gene Hackman is excellent.
9. Fight Club
The reason this isn't higher up on my list is because it's less of a comedy than everything else on the list. However, Fight Club is genius. Ed Norton's fast moving voiceover is great, and Brad Pitt gives one of his best performances. The plot is genius, but what I remember most isn't the famous twist but rather the meditation on consumerism and industry.
8. Inglourious Basterds
This is my favorite Tarentino (I find Pulp Fiction overrated; please don't hurt me) and is also the only Tarentino that I would consider a dark comedy. There aren't really any jokes in the film, instead the comedy comes from the ridiculousness of it. It totally defies history by changing the end of WWII and the Holocaust. Also, it's a genius film by making you realize that you want to see violence.
7. In Bruges
A brilliant psychological gangster drama starring Collin Farrell. It's a great film about grief and guilt. Whereas some gangster comedies films glamorize organized crime (Pulp Fiction, Lock, Stock, and Two Smoking Barrels), this brilliant gangster comedy manages to deglamorize it while staying funny.
6. Barton Fink
This disturbing story of serial murder and screenwriting is excellent. From the eerie hotel to the final scene on the beach, John Turturro's performance is excellent. He is the comedy in a film that is otherwise a disturbing drama. If you would like to see the definition of dark comedy, watch this.
5. American Beauty
The majority of this film is hilarious, but the last half hour, which takes place over the course of a day, takes a very dark and bleak turn. Kevin Spacey is one of the greatest actors in modern cinema, and this is his best role. The final scene is beautifully upsetting, and Annette Bening's performance reminds me of way too many people.
4. A Clockwork Orange
This film is wildly disturbing. It has scenes that will disgust you and change you for life. Nobody enjoys watching those scenes, but they're very vital, important scenes for the film, which is a genius satire on society. It's known for being one of the most disturbing films, but one thing that people sometimes forget is the comedy. If A Clockwork Orange didn't address the issues it does in a comedic way, then it would not be nearly as famous (or infamous, depending on your view).
The Coens strike again! Fargo, as well as number 1 on this list, is considered the essential dark comedy. It takes a disturbing, scary, violent, and, most importantly, true story and turns it into a comedy while managing to keep it realistic. Frances McDormand's performance is unforgettable, and her expression during the woodchipper scene is an incredible achievement in visual acting.
2. A Serious Man
I know, I'm overdoing it with the Coen Brothers, but, in my defense, they are fantastic directors whose main genre is dark comedy. A Serious Man is not only my favorite Coen Brothers film, but it's also my favorite film on the list. The only reason it's not number 1 s because I feel like it doesn't represent dark comedy as much as my first choice does. But A Serious Man is a very underrated masterwork about Judaism, faith, punishment, justice, and the '50s. Wonderful and hilarious, a must-see for anyone who wants to be disturbed in the funniest way possible. Also, Michael Stuhlbarg, the wonderful actor who is probably most known for his performance as Arnold Rothstein on Boardwalk Empire, is wonderful.
1. Dr. Strangelove, Or: How I Learned to Stop Worrying and Love the Bomb
It all comes down to this. The most known dark comedy, directed by Stanley Kubrick (who's appeared on this list more than once; see no. 4) is hilarious. It doesn't have any dark moments in it, but the subject matter itself is very dark (it's about an accidental nuclear attack). It's one-liners are fantastic ("You can't fight in here, this is the war room!") and some of the scenes stay with you forever. A must-see for any fan of comedy, film, or Peter Sellers.
Finally, here's one of my favorite scenes from the unbelievably underrated Coen Brothers comedy A Serious Man that really showcases the mood of the brilliant film as well as Stuhlbarg's acting experience.