Posted by RoAnna Sylver @RoAnnaSylver
Verified Creator. Author of the Chameleon Moon Series. A geeky goddess who digs sci-fi, fantasy, books, games, and fandom being awesome!
RoAnna Sylver

It's official. Halloween is over, and everybody's gearing up for the next big yearly bashes (or hurdles, depending on your levels of stress, cynicism, and holiday spirit). We have Bad Santa 2 on the horizon for 2017, and this year has been an extra-twisted one in and of itself for so many reasons... like the wave of worldwide clown crimes and sightings. We'll get back to that in a little bit, kids!

So, whether your year so far has been good, bad, or just plain dysfunctional, this cornucopia o' dark #comedy is sure to have a merry little something to get you through the long, dark months ahead, and give 2016 the festive/terrifying sendoff it deserves. Enjoy!

15. Bad Santa (2003)

Starring: Billy Bob Thorton, Tony Cox, Bernie Mac, John Ritter, Cloris Leachman, Lauren Graham

Gotta start with the original before #BadSanta2 comes to town.

  • Why It's Dark: Billy Bob Thornton plays the titular Santa, Willie Soke, who teams up with Tony Cox as his much-more-coherent cohort who endures the indignity of putting on a "lime green velvet elf costume, smiling for the kids and propping up [his] drunken ass every night." Together, they use their seasonal gig (and Willie's substantial safecracking skills) as a ruse to rob the malls on Christmas Eve. Sweet scam. Until Willie's slow-then-rapid self-destruction starts interfering in the form of alcohol-soaked mayhem, lewd changing room romps, senseless acts of violence, and aggressive self-hatred. And regular hatred. He needs many, many years of therapy:

  • Why It's Bright: It's funny as hell. Watching a train wreck of a downward spiral has never been more hilarious. Also, child actors are rarely actually funny, but Brett Kelly as Thurman Merman (I know, poor kid) has amazing comedic timing and chemistry with Thornton. He even gets through to Willie, who tries really hard to do the right thing for once, and get this sweet little kid his stuffed elephant. Seriously, he is a Bad Santa. But he might be kind of an okay person. He's trying, anyway. He just needs a chance. And some sandwiches.
  • You Gotta Watch It Just For: John Ritter and Bernie Mac's quick back-and-forth. Their dry-and-exaggerated contrast is brilliant, and so are their amazing expressions. We didn't have much hope for Bernie Mac being in the sequel given his character's 'shocking' fate, but they'll both be missed, anyway. Thanks for the laughs and the memories, guys.

14. The Addams Family Movie (1991)

Starring: Anjelica Huston, Raúl Juliá, Christopher Lloyd

How's your family around the holidays? Can't get much wilder than this one.

  • Why It's Dark: Uh, hello. The Addams have been Altogether Ooky since they showed up in a New Yorker comic in 1938. And last we checked (even if it was over 20 years ago) they were still doing exactly what they wanna do, and playing how they wanna play. Sometimes that involves medieval torture devices. No judgement.
  • Why It's Bright: Deathly decor aside, they're actually one of the most healthy and functional TV families we've ever seen. Their familial loyalty is heartwarming, Gomez and Morticia's passion remains alive and kicking after a lifetime together, and everyone genuinely supports and cares about one another. Any one of them would die to keep each other safe. Honestly, please, let them die for one another. They'd probably love it.
  • Watch It Just For: The Mamushka dance/knife-throwing scene. I swear, on Mummy and Daddums, it'll light up your life, WITH A HEY AND A HEY!

13. Mystery Men (1999)

Starring: Hank Azaria, Ben Stiller, Janeane Garofalo, Geoffrey Rush, William H. Macy

  • Why It's Dark: Greg Kinnear is Captain Amazing, the world's greatest superhero. Or...was. Was the world's greatest superhero. Now he's turned inside-out by a super-death-reactor-ray, and we get to watch it happen. The toggle switches were confusing. Sorry.
  • Why It's Bright: "We're not your classic heroes. We're not the favorites. We're the other guys. We're the guys nobody ever bets on." And they try so hard. Seriously, at its heart, this zany movie is really about everyday people, several of whom have either fail-tacular superpowers (Spleen, please stop) or none at all (what is Mr. Furious' power again?), just trying to do the right thing. Isn't that what makes a hero after all? Then there's this, one of the funniest team audition montages ever.

Did you like muscle-arm guy with the black cloak? Why they didn't let him onto their team, I'll never know.

  • You Gotta Watch It Just For: The retroactive movie star recognition. We are talking Zoolander-level levels of celebrity cameos (how many did you see up there? Hint: a lot) - except a lot weren't big stars yet! But here they are, young'uns, playing some truly out-there, bizarre, fun-as-heck roles. Kel Mitchell is Invisible Boy (he's only invisible if nobody's looking at him!). Geoffrey Rush plays a supervillain called Casanova Frankenstein, come on. Eddie Izzard is the leader of a gang of Evil Disco Boys. We got Janeane Garofalo carrying around her father's skull (his flying, telepathic, trash-talking, bad-guy butt-kicking skull) in a bowling ball. William H. Macy shovels very well, Lucille. Like the weirdly future-predicting credits song says, this movie was full of All-Stars before any-body told Shrek a thing.

12. Mars Attacks (1996)

Starring: Jack Nicholson, Glenn Close, Annette Benning, Pierce Brosnan, Danny DeVito

  • Why It's Dark: It's Tim Burton, this time with aliens. About as much death as his usual, though. Less corsets, more rayguns. And these alien invaders are mean. They're just... not nice. They don't come in peace at all!
  • Why It's Bright: There's a lot in here I don't even want to spoil, but I will say that you'll never look at a chihuahua the same way again.
  • You Gotta Watch It Just For: The best alien-conquering secret weapon ever, or maybe the worst. At least, the most relatable reaction to Slim Whitman. But it's spoiler-tastic, so you gotta see for yourself! Thanks, #TimBurton!

11. Young Frankenstein (1974)

Starring: Gene Wilder, Marty Feldman, Cloris Leachman, Peter Boyle, Teri Garr

  • Why It's Dark: "Destiny! Destiny! No escaping death for me!" That was the sound of a desperate man caught in a nightmare, struggling to escape the weight of his terrifying ancestry. When he wakes, his reality is just as frightening. Seriously, if you think too hard about the situation, it's hard not to just feel bad for everyone. (Especially the poor Creature. It's not his fault he's a little Abby-Normal.)
  • Why It's Bright: Fortunately, everyone's performances do an amazing job of keeping it light, quick, and brilliantly funny. My gosh, pick a line, the entire movie is essential to the comedy genre. If an alien landed on Earth and asked, "What is this thing called 'Comedy?'" I'd tell them, "Walk this way. No, walk... this way!"

  • You Gotta Watch It Just For: If you're blue and you don't know where to go to, why don'cha go where fashion sits?

Super-duper.

10. Beetlejuice (1988)

Starring: Michael Keaton, Alec Baldwin, Geena Davis, Jeffrey Jones, Catherine O'Hara, Winona Ryder

  • Why It's Dark: These poor, young, innocent small-town American Dreamers. First they don't know they're dead, then they finally figure it out, then they find their way to the other side, and it's a freaking government waiting room in the underworld. They have to fill out FORMS. Just kill them again already. And poor Lydia! She's so painfully lonely, all this poor girl wants is a friend. Or maybe a new family, one who actually appreciates her 'strange and unusual' wonderfulness. And then there's this guy... you know the one...
  • Why It's Bright: She gets one (a friend, that is). And the poor dead newlyweds get the Happily Ever Afterlife they wanted all along. Even Lydia's snobby avant-garde artist family ends up happy and making terrifying sculptures. Everybody wins! Except the guy whose name we must never speak, at least not three times in a row.
  • You Gotta Watch It Just For: Daaaaaay-o!

One of these daaay-o's I'll pick a scene that isn't a musical number. But come on, these are just too good.

9. The Royal Tenenbaums (2001)

Starring: Gene Hackman, Gwyneth Paltrow, Anjelica Huston, Ben Stiller, Danny Glover, Owen Wilson, Luke Wilson

  • Why It's Dark: It's a Wes Anderson film. It's going to be more bitter-than-sweet, and chock full of artfully-stylized family dysfunction. Plus, Richie's (Luke Wilson) suicide attempt is genuinely distressing. Emphasis on 'attempt,' though. It wouldn't be on this list if things got too heavy. Recovery is a beautiful thing.
  • Why It's Bright: Like I said, everything turns out okay, at least as much as possible for this particular family.
  • Watch It Just For: Seeing some damaged souls come together and be a little less damaged. Also, Gwyneth Paltrow's eyeliner.
Tell me you can't relate.
Tell me you can't relate.

Or you could always come hang with me and Julio down by the schoolyard...

8. What We Do In The Shadows (2014)

Starring: Taika Waititi, Jemaine Clement, Rhys Darby, Jonathan Brugh, Cori Gonzalez-Macuer Stu Rutherford

  • Why It's Dark: This horror-flavored story about ancient vampires fitting into modern-day New Zealand follows the beloved format of The Office, Arrested Development and Christopher Guest movies - the mock-u-mentary. This one about vampires who do everything you'd expect them to do in the shadows. Including kill, maim, and drain living victims of their vital fluids. They're aware of how gross/awful it is, too (and the film pulls exactly zero punches showing the realities and consequences of deeds done in the...you know), but it doesn't stop them from staying alive, so to speak. And when the story gets actually dark, the mood shifts seamlessly into seriously effective tension-building and well-crafted horror.

  • Why It's Bright: Aside from the above truly scary or emotionally raw parts, the whole thing is dark comedy at its finest. Even adrenaline-fueled chase scenes are mixed with sharply clever physical comedy and original visual jokes that feel fresh even to the seasoned horror or comedy viewer. It helps that the particular vampires who star in our docu-dramedy are socially-awkward, bickering, oddly endearing dorks who don't know how to use the internet their movie is on. (Until they meet systems analyst Stu! We love Stu.) But it sure is fun to watch them learn.
  • You Gotta Watch It Just For: The Vampire/Werewolf rivalry. Some shit might go down. (Like a sequel!)

7. Being John Malkovich (1999)

Starring: John Cusack, Cameron Diaz, Catherine Keener, and...

  • Why It's Dark: A down-on-his-luck puppeteer (no symbolism there, right?), played by John Cusack, finds a back-street portal that goes directly into John Malkovich's head, and discovers that unhappy people will pay through the nose for the privilege of just 15 minutes of being, well, anyone but themselves. Instead of any of the gore or eeriness you might find on the rest of this list, this unexpectedly deep movie has some overarching themes of existential sadness. These are lonely people trying to scrape together some happiness and contact in their isolated lives. Sometimes it can feel like the only way to do that is to become someone else.
  • Why It's Bright: This one is less straight-up dark, and more... weird. Really weird. I've heard a few more out-there movie premises, but most of them played midnight showings and required audience participation. Come to think of it, that's kind of an amazing idea for this one.
  • You Gotta Watch It Just For: Malkovich, Malkovich Malkovich! Malkovich, Malkovich! Malkovich? Translation: The extra-trippy sequence where the titular man of the hour gets into his own head, and... I mean, the whole thing's pretty trippy. But now everything just gets turned way up to eleven, and - I really can't even type that name one more time, just see for yourself.

6. Shaun of the Dead (2004)

Starring: Simon Pegg, Nick Frost, Kate Ashfield, Bill Nighy

That's public transportation for you...
That's public transportation for you...
  • Why It's Dark: It's a zombie movie. And by that I mean, it's not just spoofing zombie movies (although yes, yes it is), Shaun of the Dead is also a pretty dang good zombie movie in itself. It's a fond homage to the genre and retains our established horror traditions, which means we got some actual scares, some emotional gut-punches, and a lot of gore.
  • Why It's Bright: If you like the above - and a combination of quick physical comedy and dry/witty-banter style dialogue... you're gonna have yourself a real good time. You'll feel alive. So don't stop now.
  • You Gotta Watch It Just For: Speaking of...

Can't fight an undead menace without Queen!

5. Jawbreaker (1999)

Starring: Rose McGowan, Rebecca Gayheart, Julie Benz, Judy Greer

  • Why It's Dark: Well, gosh, sweeties, murder always is. If you like Mean Girls, but just didn't think the Plastics had enough homicide in their schedules, don't worry. Jawbreaker had them beat by about a decade (and Heathers before that). When three uber-popular socialites 'kidnap' a fourth for her birthday, stuff her in a trunk and silence her with a jawbreaker, she chokes... to death. Rose McGowan (the ruthless Courtney) wastes no time in covering it up - and seems oddly pleased with this turn of events. Accident, or rival-offing plot? Courtney reigns as truly evil teen royalty, and as the lament in this movie goes, "She's only in high school!"

  • Why It's Bright: High school was rough on a lot of us, I think. High school is brutal, and sometimes popularity politics can seem like matters of life and death. Here it's just a little more literal. And there's something about seeing our archenemies blown up larger than life on the big screen - then get taken down (which happens, I promise) in a spectacle that's both dramatic and therapeutic. Revenge is very, very sweet. As is the adorably nerdy Fern (Judy Greer), the murder witness who Courtney grants with a makeover to ensure her silence. Fortunately, some things (like human lives) are worth more than popularity.
  • Watch It Just For: A truly weird cameo from Marilyn Manson, which comes right out of nowhere and is never mentioned again. (He was engaged to Rose McGowan at the time, so that explains it somewhat. Doesn't explain the God-awful porn-stache, but we're supposed to be skeeved.)
...It worked.
...It worked.

4. Reefer Madness (2006)

Starring: Kristen Bell, Christian Campbell, Alan Cumming, Neve Campbell, John Kassir, Robert Torti

OH, SO MAD!
OH, SO MAD!

This movie-musical is a parody of the old, over-the-top, hyper-patriotic, Red-Scare-mongering 1950s public safety films. That stuff will make you kill your whole family, run naked down the street, and hallucinate orgies about the satyr-god Pan doing inappropriate things with large torches. Now let us tell you the story about a good boy Jimmy who found it out the hard way...

  • Why It's Bright: For all the darkness, it's genuinely sweet how much the good characters care about the innocent kids caught up in this mess, and try so hard to protect them. Even Jesus and Joan of Arc! Listen to, Jesus, Jimmy! Trust the man with the stigmata! (You Gotta!)
  • You Gotta Watch It Just For: Alan Cumming playing a concerned citizen - a very patriotic and heterosexual American one, mind! - warning a worried Parent-Teacher Association meeting against the evils of marijuana. If this were made now, Stephen Colbert would probably be cast in this role for sheer typecasting and iconic name-brand recognition, but I still can't see anyone nailing this song quite like Cumming does. That note at 2:30. That "Ohhhh." Ohhh, yes!

No, the entire thing doesn't take place in black and white, just the first 5 minutes or so. Think Wizard of Oz... on some kind of drug. (Did you catch the "Thriller" dance at 2:05? Ooh, yeah!)

...And remember that satyr I mentioned earlier? Well.

Yes, this would be that same Very Concerned Citizen. He cares about your patriotic well-being. Do it for America.
Yes, this would be that same Very Concerned Citizen. He cares about your patriotic well-being. Do it for America.

Told you this one was fun.

3. Drop Dead Gorgeous (1999)

Starring: Kirsten Dunst, Kirstie Alley, Ellen Barkin, Denise Richards, Amy Adams

  • Why It's Dark: Hoo boy, if you ever thought there was drama going on behind the scenes of beauty contests? You were so right. What horrors lie behind those Vaseline smiles, those bright lights and sequins? Blackmail, bribery, secrets, Mafia-style double-dealing... and murder.
  • Why It's Bright: It's freaking hilarious. I've brought up Christopher Guest movies a few times, and the way Best In Show skewers dog show competitions and A Mighty Wind more gently pokes at folk music stardom, this is the dark side of beauty queen politics, pageantry, and cutthroat ruthlessness taken to homicidal extremes. Maybe funniest if you're familiar with this subculture's world, but even if you aren't...
  • You Gotta Watch It Just For: Jesus on Wheels. It's just too good to be true. Can't take your eyes off of... Murderous teenage beauty queen Denise Richards dancing around serenading a crucified Jesus doll. I'd apologize for this hellraising content, but I'm laughing/crying too hard. If it makes you feel any better, she gets blown up in a freak giant swan-float accident (really) about ten minutes later.

2. Little Miss Sunshine (2006)

Starring: Alan Arkin, Steve Carell, Toni Collette, Greg Kinnear, Abigail Breslin, Paul Dano

  • Why It's Dark: This is a dysfunctional family full of damaged people. Steve Carell (in one of his most heartfelt dramatic performances) plays an emotionally-tortured Proust scholar whose attempted suicide immediately precedes this whole adventure. Then there's Grandpa... in the trunk of the car. Yeah, this movie gets dark.
  • Why It's Bright: Look at that cutie pie. Abagail Breslin is legitimately great as the sweetly awkward but determined and courageous Olive - and her family ultimately does put aside their differences and personal struggles to get her where she belongs. The spotlight.
  • You Gotta Watch It Just For: She's a super-freak! Super-freak! She's super-freaky!

Get it, Olive! Show your family that their ordeal has been worth, and their real Little Miss Sunshine was right in front of them all along! Now, all of you, on your feet! Give this little girl a shining moment in her bizarre, will-definitely-be-talked-about-in-therapy-many-years-later childhood! Everybody, dance!

1. Shakes The Clown (1991)

Starring: Bobcat Goldthwait, Julie Brown, and ....SPOILER:

  • Why It's Dark: I told you we were sending off 2016 in style. Hope you like clowns! This is the story of an alternate all-clown reality: you got your TV clowns, your Rodeo clowns... and your universally hated mimes. Our hero Shakes is a very Bad Santa-esque dude who just wants to scrape by, hang at the bar with his clown posse - and get totally seltzer-faced, embrace sweet, liquor-soaked oblivion, and forget he's a clown at all. And maybe, if there's time at the end of the night, win the heart of fair bowler Judy. (Everyone asks, 'what's an awesome gal like her doing with this Bozo?' And at the beginning... yeah, try harder, Shakes. At everything, but especially her.) But unlike most clowns you'll see haunting the streets this year, he really does have a heart of gold, and might actually have a chance for the big time.
ARE YA READY, SHAKES? (You'll get that in a minute, kids!)
ARE YA READY, SHAKES? (You'll get that in a minute, kids!)

...If nobody frames him for a cocaine-frenzy murder spree or anything, that is. That couldn't possibly happen, right? Nah!

  • Why It's Bright: ...Hoo boy, that's a toughie. We got a live one, ladies and germs, and our hero Shakes is a troubled soul with a checkered past, and an acute alcohol problem that actually isn't played for laughs. In fact, this becomes a pretty serious plot element at one point. Separate from the coke-dealing rodeo clown and villain entirely, too. Lots of substance abuse in clown land, and apparently it's one thing they take seriously. Luckily, you can't keep a good clown down for long. He's got some good friends (including a very young Adam Sandler!) who pick him up when he's down, and fight like Hell to keep him on the straight and narrow. Say what you will about clowns, the love is real.

  • You Gotta Watch It Just For: ARE YA READY, '90s KIDS? Are ya ready to see and hear Tom Kenny before he lived in a pineapple under the sea? Are ya ready to feel the cold fingers of dread creep into your soul, as one of the most disturbing and forgotten - maybe that's for the best - movie clown-villains with the voice of Spongebob Squarepants gives you nightmares for the rest of your natural-born life?

Congratulations, Binky the Clown, you are the face of this strange, frightening year. Say hello, 2016. It's you.

BONUS: An anonymous Robin Williams as a gosh-darn mime. Will a Mr. Marty Fromage please stand up? (Nice nom de plume, Mr. French Cheese. But seriously, man, we miss you.)

The Mime/Clown rivalry is ages old. Mime Jerry's got a beef... and I think he smells some right here in his class. Part hilarious, part terrifying. MIME JERRY, take it away!

Do you have a favorite dark comedy that didn't make the list?

Did you re-discover an old fave here, or are you going to rush out to make a new friend (or frenemy)? Do you know a twisted rib-tickler you think shouldn't be missed? As you might have guessed, that's kind of my jam. Sound off in the comments!