While most mainstream comedic films are light, bubbly and utterly devoid of cold, brutal, soul-crushing deaths, Hollywood has also made its fair share of black comedies. Ideally, these dark farces would strike a tonal balance that favors laughs, but the occasional failure strikes as the scales dip a tad more toward ghoulish than hilarious. And we’re not just talking about the existential horrors lurking in Carrot Top’s filmography; there’s also…

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5 ‘Duplex’

While the trailers made it seem like merely a wacky Comedy showcase of Ben Stiller and Drew Barrymore playing a married couple contending with a bad neighbor (who happens to be a little old lady), 2003’s Duplex is shockingly macabre. Yes, once they have exhausted all other avenues, the newfound homeowners turn to homicide and hire a hitman to take care of the troublesome senior. The scene in which Stiller and Barrymore describe their graphic murder fantasies to one another while gentle rom-com piano music plays is next-level chilling.

Oddly enough, this is the second comedy that director Danny DeVito made about bumping off an elderly woman. 

4 ‘Observe & Report’

Presumably traumatizing any family who showed up to the theater expecting Paul Blart-esque hijinks, Observe & Report was basically a remake of Taxi Driver but with an unrelentingly unpleasant mall cop who wants to take down a local flasher. It’s the rare Seth Rogen vehicle that takes an uncomfortable look at toxic male rage and includes a scene in which the Knocked Up star randomly beats the shit out of Patton Oswalt.

3 ‘Very Bad Things’

A dark comedy so pitch black you’ll need a miner’s helmet while watching it, Peter Berg’s Very Bad Things makes the bachelor party in The Hangover look like Easter brunch at Ned Flanders’ house. The Movie begins with the inadvertent death of a stripper and quickly spirals into a severed-limb-filled mess. This film features some of the most grotesque scenes ever committed to film featuring Jeremy Piven, which is saying something, considering that there are eight seasons and a movie of Entourage out there.

2 ‘Art School Confidential’

Art School Confidential was the highly-anticipated second effort from the creative team that gave us Ghost World: director Terry Zwigoff and writer Daniel Clowes. Based on a graphic novel by Clowes, the quirky comedy about a first-year art student also features a subplot involving a serial killer known as the “Strathmore Strangler.” 

By the end of the movie, the switch flips from lighthearted satire to bleak nightmare as (SPOILERS) our protagonist, Jerome, tries to kill himself and is only prevented from doing so by the police, who then arrest him for the murders. Though Jerome is innocent, he pleads guilty and goes to prison. Why? Because the notoriety of being a serial killer is apparently the only way to sustain a career in fine art.

1 ‘Weekend at Bernie’s II’

Weekend at Bernie’s found a couple of wannabe yuppies puppeteering their rich dead boss’ corpse around a swanky beach house to get a free vacation, which presumably every one of us would have done if in the exact same position, right? But the wildly unnecessary sequel Weekend at Bernie’s II took things to an even more screwed-up place.

For one thing, the movie begins with Bernie’s corpse being stolen from the morgue, then reanimated via Voodoo in the bathroom of a porn theater. Next, Bernie’s festering corpse is shoved into a suitcase, munched on by a shark and shot through the head with a speargun — but somehow, this doesn’t stop it from getting to second base with an unsuspecting vacationer. 

It’s like if you made a gross Megazord out of 12 different Law & Order: SVU crimes.

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