10 Great Dark Comedies From The 2000s You May Have Missed

6. Pretty Persuasion (2005)

Pretty Persuasion

At the exclusive Roxbury, a Beverly Hills high school for the wealthy, Kimberly Joyce (Evan Rachel Wood) is a 15-year-old with dreams of being an actress. When her high school drama teacher Percy Anderson (Ron Livingstone) humiliates her best friend Brittany, she hatches a plan for revenge–by publicly accusing the teacher of sexual harassment. Setting off a firestorm in both the school and the media, Kimberly watches with delight as her plot begins to pay off.

This doesn’t sound like a comedy, but it is–a very dark one. The entire tone of the movie follows Kimberly, who’s a diabolical schemer bordering on sociopathy. Wood gives a fantastic performance as the duplicitous character, one that admires a school shooter and dreams of stardom no matter what. With few likeable characters, finding refuge in audacity and profanity, and with a mean streak that barely lets up throughout, Pretty Persuasion is like Mean Girls on black tar heroin.


7. Behind the Mask: The Rise of Leslie Vernon (2006)


In a world where the slasher characters of horror films–Michael Myers, Freddy Krueger, and Jason Vorhees–actually exist, a documentary crew follows Leslie Vernon, a surprisingly genial psychopathic killer seeking to join the ranks of these legendary figures. As the crew documents his preparations and day-to-day life, Vernon explains that he’s going to slaughter a group of teenagers in his parents’ old house, complete with a “survival girl” to face him. But the documentary crew eventually realize that they can’t just stand by and let him go through with it. Or was this all part of his plan?

This clever black comedy horror film works on meta-humor and depicts a world where horror movies are real and how being a murderous monster is a trade people ply. A unique take on the horror film that features cameos from some well-known horror movie stars, the character of Leslie Vernon deconstructs the time, preparation, and thought that goes into picking out the right group of people to slaughter and setting up the killing space. A strong recommend for horror fans that know every trope of the genre and can appreciate the dark humor inherent in horror films.


8. I Love You, Phillip Morris (2009)

I Love You Phillip Morris (2009)

Truth is stranger than fiction, and I Love You, Phillip Morris is one crazy true story. Following the true story of Steven Jay Russell (Jim Carrey), a once-married but closeted gay man who–after a severe car accident–decides to start living an openly gay life. Becoming a con man, he’s sent to prison for insurance fraud and falls in love with fellow inmate Phillip Morris (Ewan McGregor). And then the story gets twisted, involving Russell escaping from prison multiple times, posing as Morris’s lawyer, and faking illness just to be with Morris.

This unbelievable true story is directed with flair and has a cheery manic tone to it. Carrey pulls back his normally unrestrained comedic performance as Russell to great effect while McGregor plays Morris with a confused sweetness. Finding humor and even romance in ostensibly wildly criminal activities, I Love You, Phillip Morris is a twisting, turning comedy that is surprisingly sweet–when it’s not being completely nuts.


9. World’s Greatest Dad (2009)

World’s Greatest Dad (2009)

Not every parent gets the kid they want or even could have expected. This is the plight of single father and high school English teacher Lance Clayton (Robin Williams), an idealistic writer and sensitive teacher who nonetheless is stuck with a rude and rather idiotic son Kyle. That is, until Kyle accidentally kills himself while practicing auto-erotic asphyxiation one day.

Instead of making his crude slob of a son’s death a humiliating joke, Lance writes a moving, sensitive masterpiece of a suicide note and claims it as his son’s, which garners great acclaim and a new understanding of who his son is–even though it isn’t. Forging a masterful journal that he purports is his late son’s and gaining the attention of the media, Lance finds respect and admiration from his students and fellow teachers–but how long can he deceive everyone?

This pitch-black dark comedy was directed by Bobcat Goldthwait and features one of Williams’ best late-career final performances. If you like your comedy extra black with a dollop of satire, World’s Greatest Dad is for you.


10. A Serious Man (2009)

Larry Gopnik is experiencing the worst few days of his life: his family’s falling apart: his wife suddenly announces she’s divorcing him for someone else; his son is supposed to be studying for his Bar Mizvah but spends his days stoned out of his mind instead; and his daughter steals money from his wallet. Even worse, at the college he teaches at, a student is simultaneously attempting to bribe him for a passing grade and threatening to sue him for defamation if he refuses. He’s kicked out of his house, moves into a crappy motel room that he shares with his brother, and finds out somebody is sending letters to the college urging them to deny him tenure. And then it gets worse.

Can you expect anything less from the Coen Brothers than to make a series of extremely unfortunate events in a relatively innocent man’s life into a comedy? A Serious Man both baffled and impressed critics with its nihilistic tone and Job-like allegory. A surprise hit for the Coen Brothers, A Serious Man is also highly divisive among their fans, with some claiming it their best work while others dismiss it as too bleak to be considered funny. But that’s the bitter pill you have to swallow if you’re going to watch a dark comedy: that it may not always be pleasant, and the laughs often come shortly after gasps.

Author Bio: Mike Gray is a writer and academic whose work has been featured on numerous websites and maintains a TV and film blog at mikegraymikegray.wordpress.com.