The Tooth Hurts

Just like with eyes, fingers, toes and testicles, teeth are an extremely sensitive part of us that we can't bear to see get broken or pulled out, whether our own or other people's. Just like with fingers, we have so many of them, giving us so many ways to feel the pain (even worse if a Depraved Dentist is involved). However, someone may pull a tooth for a good reason, i.e., it gives them so much pain.

Keep in mind that this is about teeth getting hurt or removed in ways other than getting knocked out in a fight. There already exists a separate trope for that.

Examples of The Tooth Hurts include:

Advertising

The Cliche Family (a parody ad made as an in-house demonstration) shows a little boy brushing his teeth all day, day after day, until they're almost completely worn away.

Anime

One episode of Kirby: Right Back at Ya! centers around King Dedede and Bun/Tuff getting cavities due to not properly brushing their teeth, and both of them are too scared to go to the local doctor. Dedede eventually orders a properly-skilled dentist Demon Beast to fix his tooth for him, though hearing that it doesn't use anesthetic scares him off again.

Comic Books

In Detective Comics #832, a villain named "Shark" pulls out his own teeth with pliers to plant them as fake evidence of his supposed death by sharks. He mentions that it was very painful, but he's got lots of teeth (three rows!).

Film

In Cast Away, Chuck is having a problem with his tooth in the beginning of the film, which gets worse once he becomes stranded on an island. Eventually, he knocks it out with an ice skate found in one of the packages washed ashore, but passes out from the immense pain.
I Spit on Your Grave also features a torture scene using this.
In Moon, Sam starts losing his teeth (and vomiting blood) as his short-lived clone body breaks down.
In The Pink Panther Strikes Again, the Big Bad (former Chief Inspector Dreyfus) gets a bad toothache and sends for a dentist. Clouseau pretends to be the dentist and performs dental malpractice on Dreyfus.

Dreyfus: He has pulled the wrong tooth! There's only one man who would pull the wrong tooth. It's Clouseau! Kill him! Kill him!

There was a scene in Finding Nemo where the dentist was trying to remove the prime minister's tooth. When Nigel the pelican runs into the window, the noise startles the dentist so much that he forcefully pulls out the bad tooth, putting the prime minister in a lot of pain.
Also used in a Three Stooges short when Curly gets a toothache.
- A number of Stooge shorts involve teeth being pulled or smashed out, often painfully. It's often the wrong tooth that is yanked, or even the wrong person getting yanked.
In Saw VII, a character learns that the combination to get through a door has been etched on two of his teeth. He must extract them with a pair of locking pliers in order to proceed.
- In an early draft of Saw III, some of the chains holding Troy in place for his trap were hooked through his teeth, requiring him to pull them out if he wanted to free himself. One of the movie's posters displayed three uprooted teeth dangling from wires as the Roman number III.
In Oldboy, the protagonist tortures one of his tormentors by performing dental surgery with a claw hammer.
In X Men: First Class, Erik Lehnsherr uses his powers of magnetism to forcibly extract a Nazi sympathist Swiss banker's metal fillings as an interrogation method.
The Laurel and Hardy silent Leave 'Em Laughing involves Stanley getting a toothache.
In Chronicle, Andrew, slowing slipping into despair-induced madness, uses his telekinetic powers to yank three teeth out of a bully's mouth. For added horror, he later shows off the teeth to his camera, absent-mindedly noting that he was able to get the first one out cleanly, but ended up actually breaking the other two.
In Marathon Man, Szell drills into one of Levy's teeth every time he gets an answer he doesn't like.
In District 9, Wikus loses two molars about 40 hours after being exposed to the alien fluid that turns him into a prawn. One he loses when chewing food, the other he pulls out himself.
One of the many unsettling sex scenes in A Serbian Film involves a woman who has her teeth removed.

Literature

In her book My Most Secret Desire, Julie Doucet recounts a dream in which her teeth were falling out.
In Dune, one character forcibly removes a tooth from another character and installs a fake tooth. It's not done for torture purposes, but it's obviously excruciating.
In The Adventures of Tom Sawyer, Tom has a toothache and his Aunt Polly decides the tooth has to come out. She ties one end of a string to the tooth and the other end to a bedpost, then frightens Tom with a hot coal. When Tom jerks away, the string yanks out the tooth.
Stanislaw Lem's short story "Highest Possible Level of Development" in The Cyberiad had a drug, Altruzine, that caused tele-empathy. A man with a toothache has the painful tooth ripped out by nearby people who don't want to feel his pain.
This plays a part in the Dick King-Smith children's book The Stray, since the main character has a fear of dentists but starts developing tooth pains partway through the book.
One story by Wilhelm Busch uses this trope. Hilarity Ensues (well, for the reader). You can read it online here (in German).
Edgar Allan Poe's short story "Berenice" is about a young man with a tendency to go into trance states where he can't remember his actions afterward and a growing obsession with the teeth of his cousin/fiancée Berenice. Eventually he wakes up from one such state, surrounded by bloody dental implements and holding a box full of Berenice's teeth.
In Nineteen Eighty-Four, O'Brien rips out one of Winston's teeth with his hand, to show him that he's "rotting away" and "falling to pieces".
A Song of Ice and Fire: Pia's teeth are bashed in by Gregor Clegane for speaking out of turn, ruining her pretty face. Even more deliberately, Theon's teeth are destroyed to the point where chewing is nigh impossible because his tormentor didn't like his grin.

Live Action TV

On Malcolm in the Middle, Hal hurts his tooth while eating some snacks during a poker game, and one of his friends who works as a dentist treats it. However, after getting a huge bill (when he assumed it would be free because the friend said something along the lines of, "I'll take care of it"), Hal eventually rips out his tooth as protest, but passes out. He spends the rest of the episode swallowing his food whole.
One of the methods of the Sadistic Dentist of Asian Persuasion from Alias.
One of the regular sketches on Turkey TV was "Dental Nightmares", featuring a Depraved Dentist willing to pull all of a patient's teeth out in response to the smallest dental problem. Some of these he even causes.
In the Supernatural episode "Malleus Maleficarum", a witch uses magic to make a woman's teeth fall out. An episode earlier, Dean narrowly escaped having a tooth pulled out as part of a pagan ritual.
In Chuck, as part of a If You're So Evil Eat This Kitten proof of Chuck being a cold-blooded torturer, he is forced to torture Casey. He extracts a tooth to extract information. As it turns out, Casey needed that tooth pulled anyway and thanked Chuck for saving him a trip to the dentist.
Fred Sanford once went to great pains to avoid the dentist when troubled with a bad tooth, even specifically requesting a black dentist to treat it.
Al Bundy's teeth are so disgusting and yellowed even a dentist is appalled at the look of them.
In Sabrina the Teenage Witch, the title character was confronted with a security guard while going to a rock-concert with a few of her friends, when the guard couldn't let them in, Sabrina casts a spell which causes his teeth to fall out, the guard notices it and runs off, he is never mentioned again, which also makes him a Victimized Bystander.

Music

The subject of "The Interfaith Dental Clinic" story Townes van Zandt tells on the album Together at the Bluebird Cafe.
"Cavity Search" by "Weird Al" Yankovic is all about an unpleasant visit to the dentist, which includes extractions and drilling.

Music Videos

The video of Green Day's "Geek Stink Breath" has scenes of a very gruesome dental surgery.

Newspaper Comics

Played for Laughs in Beetle Bailey, where jokes about General Halftrack losing his dentures are common.
Garfield:
- In this old strip, Garfield loses his entire set of teeth trying to open a bottle with his teeth. (Word to the wise, Don't Try This At Home.)
- A similar joke occurs in this strip where Garfield tries to eat Jon's leftover pizza.

Theater

Orin Scrivello, DDS from Little Shop of Horrors (and its film adaptation) takes great delight in having to pull teeth, as well as anything else that inflicts pain on his patients. He even gets a song about it.

Toys

The Play-Doh "Dr. Drill and Fill" playset lets the kids fill, drill or extract their plastic patient's teeth.

Web Video

In his review for The Simple Wish, The Nostalgia Critic was nice enough to show his Eternally Pearly-White Teeth being shattered at Mara Wilson's cutesy child acting.

Western Animation

This plays a part in a Rugrats episode, where Angelica is trying to pull out one of Chuckie's teeth for tooth fairy money.
In the Phineas and Ferb episode "Bubble Boys", during Dr. Doofenshmirtz's attempt at country-western singing:

Audience Member: This stinks so bad I wanna break somethin'!
(He grinds his teeth together and they shatter with the sound of glass breaking.)
Audience Member: ... Yeah, that really wasn't worth it.

In Dexter's Laboratory, one episode of the Justice Friends has them trying to avoid the dentist from fear of this. It's subverted: Krunk, the Hulk Captain Ersatz, only got a tortilla chip in his tooth—which just needed a simple, painless extraction—compared to all the idiotic stuff Major Glory tries to do to his tooth. The Aesop: Go to the dentist, or it'll hurt MORE (which is actually a pretty good Aesop).
My Little Pony Friendship Is Magic: In "The Cutie Pox", Apple Bloom trips over a root and chips a tooth. Fortunately, Zecora has the skill to prepare a dentistry potion.
In Tennessee Tuxedo and His Tales, Chumley got rather destructive in his pain-induced rage. Yet even after encouragement from the ever-informative Mr. Whoopie, he was hardly willing to see a dentist.
In Muppet Babies, Fozzie's tooth pain got him sent to the dentist. The rest of the gang shared his fear and felt for him.
Older Than Television example: Bosko's dog Bruno ate too many brownies. The visual metaphor didn't help matters.
An extra gruesome episode of The Ren and Stimpy Show showed why it pays to brush teeth.
Many MGM and Warner Bros. cartoons show a hungry predator unwittingly biting down on something hard they think is food or prey and smashing out all their teeth.

Real Life

Pulling your teeth hurts, as hundreds of screaming children attest.
- Nowadays, injecting the anesthetic is the hurty part. Then half your jaw feels "jammed" and you almost don't feel the teeth being pulled. However, you are screwed if it's wisdom teeth being pulled- if they're lodged in there pretty good,and especially if they're not oriented straight up-and-down, it can hurt even if your jaw is pumped full of anesthetic.
  - This is the main reason many people opt to be put under during the actual surgery. However, even afterwards there is pain in the area (usually, pain pills are prescribed), sometimes accompanied by bruised cheeks, sores around the corners of the mouth, or a particularly nasty condition called dry-socket.
    - There is some good news, though - apparently, a new type of drill that makes the injection less painful is being developed.
Tooth cavities, or worse, tooth abscesses.
Chipping a tooth, if you lose enough it'll expose the nerve causing all kinds of pain.
Considerably less severe than the other cases presented, but newly-applied braces can leave one with the entire mouth feeling sore until the teeth get used to the unrelenting tension.
- Not to mention bleeding and possible inability to eat solid food till the soreness goes away.
Sudden heat or cold can be painful, especially if your teeth are more sensitive.
And it only gets worse in the history books!
Pulling the pin from a grenade with your teeth is never a good idea in real life. It's a great way to break or even yank it out.
A famous story in the news recently consisted of a jilted dentist pulling all her ex-boyfriend's teeth as revenge.