Movies like Heathers or Fargo? What's there 2012 equivalent? Maybe I'm just missing them but I honestly can't think of any right now. Killer Joe, maybe?

Seven Psychopaths for one.

In Bruges (2008)
Four Lions (2010)
God Bless America

yes.

HOrrible bosses?

Tyler Perry makes dark comedies.

Yeah PopcornTreeCT..... Killer Joe. It fits the bill. In spades.

Couple years old, but my first thought was "The Ice Harvest" (2005, John Cusack & Billy Bob Thornton).

I thought that was more of a straight up comedy.

Killer Joe definitely. I'll never look at fried chicken the same way.

I didn't know FARGO was a considered a comedy. I liked the movie a lot but I don't think I ever laughed watching it.

Fargo is as much a drama as it is a comedy, but it's got a certain tone that might not resonate with everybody. Parts of it have me in hysterics. Like the interchange in the car where Buscemi challenges Stormare to converse more and he treatens to give him the silent treatment but is totally incapable of shutting up. The discomfort is half the comedy there but a lot of people wouldn't like that.

I think most dark "Dramedy" type content has been turned into TV shows lately, like Breaking Bad and Shameless. Killing Them Softly looks like it might be mildly comedic. Seven Psychopaths. Get the Gringo.

Not recent but Scotland, PA fits the category as well.

You missed out on half the fun of the movie. Did you laugh during "Raising Arizona?"

Burn After Reading was equally hilarious and shocking. Especially THAT moment (Brad Pitt's dopey grin)...

I'd say Observe and Report was a fairly dark comedy at times.

As long as Todd Solondz is still working, yes.

Isnt there a sequel to Bad Santa in the works? That would count.

A few years ago, I liked the movies PLANET TERROR, 300, and PUNISHER WAR ZONE precisely because they were filled with black humor. I don't know if that's what you were looking for, though.

More recently, I considered BRIDESMAIDS and YOUNG ADULT dark comedies.
One (BRIDESMAIDS) was more successful (at making me laugh) than the other.

that's for sure. Palindrones...that movie bothers me.

I've always considered Pulp Fiction a comedy. The lines are hilarious.

Pulp Fiction works but that movie is nearly 20 years old.

Every Coen Brothers movie is a comedy. Even No Country For Old Men. I rewatched that last week and forgot how much humor is beneth all the dread.