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10 Edgiest Quotes From Comedy Movies

Shock can be a very valuable tool in the writing of comedy. If you can shock your audience with something so outrageous that it probably shouldn’t have been said – a truly dark, edgy, close to the best joke that comes completely out of the left field – then you’ll probably get one of the biggest laughs of the whole movie. The writers who have always been the best at this have been the likes of David Zucker, Jim Abrahams, Jerry Zucker, and of course, the comedy mastermind Mel Brooks. Shock humor can be very easy. If you make a joke that simply references a controversial topic, then it’s technically edgy – or an attempt to be edgy. But genuinely edgy humor is the kind that cuts right to the bone and reveals a social point or something else that is meaningful and also subtly alarming. Here are the 10 finest dark jokes from comedy movies.

10. “We call ourselves the Ladykillers,” from Anchorman 2: The Legend Continues

As far as sequels go, Anchorman 2: The Legend Continues is pretty good. It’s not great. The trouble that Adam McKay and Will Ferrell had with their sequel was that they had to at least match and hopefully top one of the most original and brilliantly absurdist movies ever made. The first Anchorman movie is genuinely one of the funniest movies of all time. It’s one of the most beloved comedies ever made with one of the biggest fan bases. Creating a sequel to Anchorman was like creating a sequel to Airplane! or Groundhog Day or Caddyshack. A lot of the jokes in the movie employ hindsight to make fun of its 1980s setting. There’s a beautifully dark moment in the movie where Paul Rudd’s character Brian Fantana says, “I got a good group of buddies out there: O.J. Simpson, Phil Spector, Robert Blake. We call ourselves the Ladykillers.” These three guys were all celebrated public figures in the ‘80s when the movie is set. But then Simpson allegedly murdered his ex-wife and her friend, Spector was convicted of murdering actress Lana Clarkson, and Blake murdered his second wife. Ah, hindsight is a wonderful thing – especially when it’s used for dark comedy.

9. “There’s a serial rapist in Crown Heights…Sorry, that’s from my other job,” from The Other Guys

The Other Guys came before Michael Keaton’s big dramatic comeback with Oscar-baiting movies like Birdman and Spotlight and The Founder. He played one of the most memorable characters in the movie – Gene Mauch, the captain of the precinct where its leading duo work. There’s a brilliant moment where Will Ferrell’s character Det. Allen Gamble is told not to refer to the Captain by his first name, so he starts calling him “Captain Gene” instead. Then Keaton perfectly delivers: “It’s not Captain Gene. I don’t have a kiddie show. That sounds creepy.” Plus, there’s all of those moments where he unwittingly quotes the songs of TLC. But the character’s best moment is also a very dark one. He has a troubled kid who’s trying to discover himself in college, so he’s had to take on a second job as a supervisor at Bed Bath & Beyond. One time, while he’s briefing his staff about the new stock before a work day, he says, “First thing’s first: the new bath mats are here. Second thing: there’s a serial rapist in Crown Heights…Sorry, that’s from my other job. Ignore that…No, wait, don’t ignore it – especially if you live in Crown Heights. Walk in pairs.”

8. “Jay couldn’t rape a fly!” from This is the End

This is the End is one of the funniest dark comedy movies of all time. It has Jonah Hill getting possessed by a demon and spewing black mucus all over James Franco and Seth Rogen. It has Danny McBride threatening to ejaculate “like a goddamn dump truck” in large deposits all over the house. It has people aiming guns and baseball bats at each other. And these are the jokes. These are the gags. And they’re all hilariously executed. If you have an inherently dark sense of humor like the brilliant comic actors who play themselves in this movie, then pulling off jokes like this comes pretty naturally. The same goes during this scene, which comes after Emma Watson shows up and they give her a bed to stay in. Jay Baruchel suggests that they need to be careful about the vibe that the six men give off around her. The others are confused about what he means, so McBride bluntly says, “He’s talking about a rapey vibe.” This leads to the guys all bickering about who is the most “rapey” of the bunch. They all decided on Baruchel, so Jonah Hill jumps in and tells them, “Guys, guys, guys. Jay’s not rapey, Jay couldn’t rape a fly.”

7. “I don’t care if we kill someone…” from The Hangover

The role of Alan in The Hangover is what made the great alternative comic Zach Galifianakis a big star. And he deserved it, too – along with Ken Jeong, he’s pretty much entirely what made that movie that instant comedy classic that it was. The character has a ton of hilarious quotes in the film, like his line about having a satchel like Indiana Jones or when he asked the receptionist at Caesar’s Palace if the real Julius Caesar lived there or, of course, “Hey, there are Skittles in there!” There is also his mispronunciation of the word “retard” in the car on the way up to Las Vegas, which is pretty edgy. But it is arguable that the edgiest line comes right at the very beginning, as Alan and the groom to be, Doug, are getting fitted for their wedding suits, ready to head off for the bachelor party. It’s the left turn that this scene takes that makes it so funny, because Alan starts off lightheartedly telling Doug that he will stick to the ethos of what happens in Vegas stays in Vegas and then takes a grave turn to say, “Seriously, I don’t care if we kill someone.” Good Lord.

6. “This is Urkin, the town rapist. Naughty, naughty!” from Borat

Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan, better known simply as Borat, is one of the most controversial comedy movies ever made. Even while they were filming it, it was controversial. The great comic genius Sacha Baron Cohen was improvising the whole thing. They shot it like an actual documentary, with all the interview subjects none the wiser, except the interviewer wasn’t a real Kazakhstani reporter – he was just a brilliant comic in character. This very shocking and very offensive (and very funny) moment comes right at the beginning of the movie, just as the title character is showing us around the town where he lives in Kazakhstan, introducing us to all of the locals. When he gets to one of them, he points to him and gleefully says, “This is Urkin, the town rapist. Naughty, naughty!” It is so unabashedly wrong that it becomes hysterically funny. People have actually been repurposing this quote lately to instead say, “This is my town of Hollywood. This is Harvey, the town rapist. Naughty, naughty!” So, even though it’s a dark and absurd joke, it actually has a real application. That’s the sad world that we live in.

5. “You guys on Myspace, or…?” from Superbad

Superbad is one of the best comedy movies in recent memory. Seth Rogen and Evan Goldberg had been working on the screenplay since they were teenagers, so it was totally refined and perfected by the time they came to actually make it. There’s a great plot development as a weird little character played by Joe Lo Truglio’s hits Jonah Hill with his car and won’t let him go to the police because of his priors, so he offers to give Hill and his companion Michael Cera a ride to a party where they can get booze. So, they hop in his car, head to the party, and on the way, this creepy dude asks them if they’re on Myspace. The genius of this scene is that it does not express tell us that Joe Lo Truglio’s character is a pedophile. It suggests it in the subtlest of ways. By asking them, “You guys on Myspace, or…?” he suggests that maybe he is a pedophile who wants to stalk these young boys, and yet he could just be a bit of a weirdo who wants to be their friend on social media. This ambiguity is where the hilarity of the joke comes from.

4. “Never go full retard!” from Tropic Thunder

Before a word even comes out of his mouth, there’s something inherently offensive about Robert Downey, Jr.’s character Kirk Lazarus in Tropic Thunder, since he’s playing a method actor who wears blackface makeup to get into the role of a black man. But then Lazarus speaks to action movie star Tugg Speedman about his maligned role in the ham-fisted Forrest Gump-esque drama Simple Jack and why he didn’t win an Oscar for it: “Everybody knows you never go full retard.” Speedman asks him to elaborate and he launches into a whole offensive monologue, “Check it out. Dustin Hoffman, Rain Man: look retarded, act retarded, not retarded. Counted toothpicks, cheated cards. Autistic, sure. Not retarded. You know Tom Hanks, Forrest Gump. Slow, yes. Retarded, maybe. Braces on his legs. But he charmed the pants off Nixon and he won a ping pong competition. That ain’t retarded. He was a goddamn war hero. You know any retarded war heroes? You went full retard, man. Never go full retard. You don’t buy that? Ask Sean Penn, 2001, I Am Sam. Remember? Went full retard, went home empty-handed.” There are a lot of offensive words in this speech, but a lot of the points raised are true. If you’re playing a character who is mentally challenged and you want to win an Academy Award for it, you shouldn’t go all out for it. Don’t make it an absurdly over the top, cartoonish portrayal. You need to bring some subtlety to it.

3. “Have you ever seen a grown man naked?” from Airplane!

The writing of Airplane! is not crass or juvenile or overly sexual. This is not a farce, it’s simply a parody of disaster movies – specifically an old corny one named Zero Hour! – that is peppered with witty jokes and intricately staged sight gags in order to wring out as many laughs as possible from the audience whose intelligence it does not underestimate, whether they have seen the source material or not. That is what the success of the whole movie rests on. But be that as it may, there is one sexual gag in the movie. And the rest of the movie is so unlike this gag that it’s what makes us laugh so much at it – it comes completely out of the left field! It sets up a pretty traditional situation with the ambitious little kid who dreams of being a pilot being allowed to have a look around the cockpit and meet the captain. It’s this wholesome nature that leads us into complete shock when the seemingly harmless captain blatantly reveals himself to be a pedophile by asking the kid if he’s ever seen a grown man naked. This is followed by increasingly unusual and homoerotic questions like “Have you ever been in a Turkish prison?” and “Do you like movies about gladiators?” This is dangerous territory for comedy, but the dream team of Zucker, Abrahams, and Zucker pulled it off hysterically.

2. “I take it black…like my men,” also from Airplane!

That’s right, there’s another entry from Airplane! on this list, for a couple of reasons: 1) it is the greatest comedy movie ever made, so it stands to reason that it would have more than one good joke, and 2) for a movie that’s not particularly dark, Airplane! has some really dark lines in it. This one stands out for insinuating that a little girl is not only sexually active, but also has a thing for black guys. It’s nothing short of a miracle that they even managed to slip this one past the distributors. And what’s so great about the gag is that it’s set up so perfectly to be a cute moment. We see a young boy trying to flirt with a young girl – it’s being set up as a sweet little romantic moment, but as we know, that’s not how Zucker, Abrahams, and Zucker operate. So, the boy proceeds to try and woo the girl with a cup of coffee (so already, there’s the absurdity of kids drinking coffee and chatting each other up just like adults), and then she completely shuts him down with this jaw-dropping line. Even the other kid’s jaw drops when she says it! The line is so brilliant, because it serves a few purposes: it takes a very abrupt left turn, it leaves the audience in a tizzy since they couldn’t anticipate what would happen next, and it cuts the scene off unexpectedly, so you’re left to just laugh your ass off.

1. “Where the white women at?” from Blazing Saddles

Talk about making light of the Ku Klux Klan! Sure, Quentin Tarantino did this a few years back with that scene in Django Unchained, but Blazing Saddles was doing it almost forty years beforehand. In his satirical western spoof about a town who has a black sheriff appointed in an attempt to run it into the ground to make way for a railroad, Mel Brooks didn’t hold back in his critique of racism. He even got Richard Pryor, perhaps the edgiest and most racially driven standup comic of all time, to get involved in the writing of the script. Pryor put so many N-words in the script that even for a movie that’s notorious for its excessive use of the slur, they had to take out way more that he had written in before they even started shooting. In one scene, the sheriff and his white companion need disguises to get into the group of bad guys, when they spot two guys from the KKK. They have to provoke them in order to steal their sheets, so the white one grabs the sheriff and tells the Klan guys, “Hey, fellas, look who I found!” and then the sheriff puts the icing on the cake by asking them, “Where the white women at?” as if he was just out on the patrol for white women, which is exactly what the KKK would think he is doing. In five words, the sheriff had summed up exactly what the KKK’s fears are, stemming from D.W. Griffith’s Birth of a Nation. The Klan members are worried that black men will prey on their white women. And in just five words, he tempts them to chase him by validating all of their worst fears and the reason for their way of life. It’s an edgy and hysterical line, but it is also a line that points out just how narrow-minded the KKK are (not that we needed reminding, of course).

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