30 Minutes or Less (2011) http://www.imdb.com/title/tt1622547/
Dwayne is a man-child, unemployed, skill-less, still living at home. He has an idea for a tanning salon as a front for prostitution but doesn't have the funds to get started. Dwayne's father won the lottery and Dwayne is worried the money will be spent before his father dies. So Dwayne and his equally-unambitious friend Travis cook up a plan to have Dwayne's father killed. The hit man will cost $100grand, so they come up with a scheme to strap a bomb to an unsuspecting pizza delivery guy and make him rob a bank to fund their hit.
If the whole 'strap a bomb to a pizza delivery guy to force him to rob a bank' sounds familiar it is because that really happened back in 2003, with an explosively tragic result, and received a lot of news attention at the time. No, this film is not a documentary nor historical fictionalized drama about that incident. The real event wasn't funny and is a unique enough incident to not really qualify as a subject of dark or gallows humor. But someone wrote the film anyway. The writers of this film claim they were either unaware of the incident, or perhaps vaguely aware of it. Dubious.
So my mindset going in to the film was one that's balancing "inappropriate comedy subject matter" on one side and a curiosity about how they pull off the film on the other.
We get a core cast of Jesse Eisenberg (Social Network, Zombieland, etc) as Pizza Delivery guy Nick, Aziz Ansari (Parks and Recreation, etc) as his best friend Chet, Danny McBride as Dwayne, Nick Swardson (you'll recognize him when you see him), Fred Ward as Dwayne's dad, Michael Pena as the hitman. Actually a pretty good cast mix.
Good thing too. The success or failure of this film rests squarely on the cast being able to pull it off. And they do. Especially Ansari. That dude is funny. I'm not a Parks & Rec watcher, so I have no idea if he plays the same type of character or not.
The comedy wavers between situational, physical and a mix of lowbrow to middle comedy. When the script first hit the lowbrow comedy beats I was worried, but as the film continued the cast performance makes up for grabbing at low-hanging fruit. The characters (and cast playing them) and situation are interesting enough to stick it out through the low bits, even though the outcome is more or less predictable.
So, even though at first blush I thought that making a comedy out of the incident somewhat inappropriate considering someone's head was blown off in the real world, I watched a film much funnier and more entertaining than I anticipated. Sure it is dark humor and trivializes the real-world incident. It isn't the first film to do that, nor will it be the last.
Edit September 2012:
Randomly encountered this film on cable the other day, ended up watching it again. Liked it again too, and was even less concerned about it's parallel to the real world incident this time. So yeah, this does have a rewatchability factor to it, even knowing how everything plays out. That's a plus.