Dr. Mizunokuchi of Speed Grapher is a monstrous dentist equipped with spider-like limbs that have dental implements on them, as well as the ability to turn body parts, such as his tongue, into drills. He likes to work slowly.
Subverted in Kirby of the Stars: When both Dedede and Bun/Tuff come down with toothaches, Dedede summons a scary-looking dentist demon-beast that works without anaesthetic... because his skill is such that he can drill out a tooth without causing pain at all. Doesn't stop the big wuss Dedede from sending him into the sky.
In one chapter of Urusei Yatsura, Ataru dreams that Lum will "help" him get over a tooth ache with some sort of dentistry torture chair.
Usagi and Chibi Usa express fear of the dentist because they describe the only dentist in town as sadistic. They are more then happy to run off to the new, fun dentist in town only to have it turn out to be a trap by the Amazon Quartet.
There's a short extra in the manga in which Usagi, Mina, and Chibi Usa decide to visit the hot new dentist for their cavities - who is secretly a minion of a ghost who gains power from cavity pain.
In episode 10, Keroro gets a cavity, and Kururu checks him out, showing an inordinate fondness for banging on the tooth in question with a dental mirror. It turns out that Keroro's cavity (and cavities in general) is being caused by a powerful race of alien invaders...who are the size of bacteria.
Robo-Keroro makes a Heroic Sacrifice, letting the rest of the team escape, and activates his "secret weapon"... which happens to be a bouquet of flowers and a few fountains sprouting out of his head. Kururu then activates the real secret weapon. Robo-Keroro is an Action Bomb. Poor Keroro (the real one) gets his mouth nuked, which blows out all his teeth, destroying the Karies base. Luckily, Keronians can regrow teeth at an amazing speed. Kururu caused Keroro pain, tricking him into causing the same thing himself. The guy loves causing others pain and misery.
In Lupin III, Jigen is afraid of dentists in general, and his worst fears were realized in the "Red Jacket" anime, where he encountered a dentist who was actually an enemy agent, who shackled him to the dentist chair and then tried to kill him with a king cobra.
Soil: New Town's council president is a dentist/orthodontist. He's an obsessive neat-freak techno-savvy voyure pedophile rapist whose victims are basically every boy who didn't want to be awake during a cavity for the past decade, has the whole town under a CCTV net, used the footage to incite the rest of the council to terrorize one family who (probably) didn't do anything, tortured one victim's mother with a drill during an exam, and killed a bunch of cats as a warning to a homeless woman who offended his sense of "purity". He later learns the hard way not to mess with people's mothers; meanwhile his victims have unknowingly banded together to destroy the world.
Averted in an Archie Comics story. When Jughead gets a toothache, his friends drag him kicking and screaming to the dentist. From the waiting room, they listen to him howling in agony until Archie decides to intervene.
Archie: Doctor! What are you doing to him?
Dentist: I haven't done anything yet. I'm just taking X-rays.
In a Don Martin MAD book, Fester Bestertester goes to see a dentist who's rather enthusiastic about the prospect of having to drill. Although the preparation causes poor Fester a great deal of pain, when the drilling itself starts he remarks that he doesn't feel a thing. "Of course not," says the dentist, "but heaven help you if it were to slow down for even a second." Fester then reveals that he hasn't come for a check-up after all, but to deliver a note which says that at 2:30 P.M. the dentist's electricity will temporarily be turned off. Guess what time it is...
Dave Berg "Lighter Side" strip in which a patient asks how much it'll cost to have a tooth pulled. When the dentist tells him, the patient protests that that's way too much for only twenty seconds of work. "We can make some sort of agreement," says the dentist with an evil grin. "I'll pull it slower!"
From the parody of the remake of "Invasion of the Body Snatchers," one of characters suspects a dentist is a pod person because, during a root canal, he drilled into a live nerve and didn't even smile.
In a Judge Dredd origin story, it is revealed that the father of the man who later became Judge Death was an extremely depraved dentist. Not only did he enjoy paralysing his patients instead of anesthesizing them, then tearing out every tooth they had, but he'd also murder them mercilessly to cure them of "brain worms". A healthy role model for the good Judge, no?
In one Far Side strip, a boy is waiting with his mother in a dentist's waiting room. Through a glass panel in the door, he sees that the dentist is actually a monster whose human face is only a rubber mask.
Invoked at the very beginning of Batman: Mad Love. It begins with Commissioner Gordon going for a dental check-up. He is literally sitting in the chair when he realizes something is... offabout his dentist. Then iron rings clamp around him, and the very next panel is of The Joker turning around to reveal himself, holding an over-sized drill that he probably intends to do very, VERY bad things with...
One of Edika's short comics tells the story of a kindly well-meaning dentist who's not the least bit worried by his constant massive nervous spasms, and the horrors he inflicts with his drill.
G.I. Joe: Doctor Mindbender is a subversion. He was a dentist before he became a villain, but a nice one. He only went nuts after he was mindwiped. (In fact, the reason he went crazy was because he invented a psychological technique to use as anestetic for dentistry and tested it on himself. It didn't work as planned...)
Scootaloo: I told you pulling teeth wasn't the answer to everything.
Sweetie Belle: *sheepish grin* I thought teeth grew back.
Scootaloo: No... No... Just... No, Sweetie Belle.
There is a Russian cartoon called Captain Pronin where the hero is captured by his enemies, and the high ranking one explains that his job is making drugs, and his hobby is inhumane experiments in stomatology. Very few managed to survive more than two fillings...
In Chiisai Shoppu, the "anime adaptation" of Little Shop of Horrors, there was Dr. Haru, who is based off of Dr. Farb from the original 1960 movie, who eventually retired to become a surgeon. A biker named Samekiba Orin, based more or less on Orin Scrivello, becomes the new dentist shortly after.
Hermione's parents torturing Death Eaters with their knowledge of dentistry is fairly widespread in the fanfic. Larceny, Lechery, and Lune Love Good is a standout example of the trope.
In the comedy The Dentist (1932), W.C. Fields wrestles with a recalcitrant patient and drags her around the room with her tooth in his pliers. One patient is so anxious she starts screaming as he tries to use the mirror tool and isn't even close to her mouth - screaming enough to send a patient in the waiting room out of there.
In the 1976 spy movie Marathon Man, former Nazi concentration camp dentist Szell (Laurence Olivier) tortures an American secret agent's brother with "oral surgery" in order to find the location of some precious gems, while repeatedly asking him "Is it safe?"
This scene from Marathon Man is parodied in Hot Shots!
In the 1996 horror film The Dentist, Dr. Alan Feinstone loses his mind after learning of his wife's infidelity and, hallucinating filthy, rotten mouths, takes it out on his staff and patients before finally being committed. He escapes to wreak further molar mayhem in The Dentist II: Brace Yourself. Loosely based on the Real Life serial killer dentist Glennon Engleman.
Willy Wonka, in the 2005 film adaptation of Charlie and the Chocolate Factory, reveals that his wacky obsession with sweets is a rebellion against his father (played by Christopher Lee), an obsessive dentist who forbade all candy and made Willy wear horrible braces and headgear. Though their eventual reconciliation shows that he was just an Overprotective Dad, rather than genuinely demented individual. Also, young Willy apparently did have some real problem with his teeth, since old Wilbur actually recognises his son from his unique dental condition decades later.
The short film On Edge starring Doug Bradley of Hellraiser fame. A patient gets er, impatient and wanders into the office ahead of his appointment to find a dentist all too willing to see him. As subsequent conversation reveals some issues in this dentist's past the patient is made painfully aware he should have waited his turn.
Subverted in Finding Nemo, where the dentist is an affable, inoffensive sort and it's his niece who's a serial fish-killer. He's still pretty incompetent, though. His patients are clearly in enormous pain when he operates on them because he's so cheerfully casual about rather complicated operations, like saying, "That's one way to pull a tooth" when he yanks one out as a result of being startled by Nigel the pelican slamming into his window. The fish seem to enjoy watching him do operations.
Kalgan's infamous "ancient dentistry" torture scene from Space Mutiny.
In the 1934 version of The Man Who Knew Too Much, Bob Lawrence and a friend visit such a dentist office in search of his missing daughter. The friend's visit behind the door of the examining room is played for laughs. He comes out nursing his jaw after having a perfectly healthy tooth pulled. Lawrence's visit is much more sinister. He struggles with the doctor, who tries to kill him, and then puts him to sleep with his own gas.
Sam Waterston's dentist in Serial Mom revels in his patients' pain, although it's supposed to be educational. Of course he's not the Ax-Crazy of the movie.
In Phantom of the Paradise, all of the inmates at the prison Winslow Leach is sent to have their teeth removed and replaced with metal ones, because of an experimental health procedure funded by the Big Bad.
Dr. Farb in Roger Corman's The Little Shop of Horrors. Unlike his counterpart from the musical, Orin Schrivello, Farb is not quite as sadistic and has a slightly smaller role, but still finds enjoyment in brutalizing patients.
Julia in Horrible Bosses is depraved in a different way than usual — her job affords her daily access to handsome men she can drug unconscious, and she takes advantage of this at least twice.
The dentist who serves as the main antagonist in She Woke Up Pregnant is also of this sort. When one of his victims winds up pregnant because of this, she decides to fight back.
Dr. Schultz from Django Unchained is a subversion. He is a former dentist turned bounty hunter, who gladly guns down bad guys for money, but he is also a deeply compassionate and highly moral individual.
Igor Peabody, from the Problem Child series of films, was the principal of an orphanage in the first installment and the principal of a school in the second. In the third, already showing a severe lack of sanity from all the headaches Junior has caused him, he becomes a dentist, and vents his frustration on his patients, but specially Junior, with whom he has a bone to pick.
Dr. Jane Payne, from the children's book series Wayside School, likes to pull patients' teeth whether necessary or not, in order to charge them more.
Mr. Croup and Mr. Vandemar, the Old Firm, from Neil Gaiman's Neverwhere. "Obstacles obliterated, nuisances eradicated, bothersome limbs removed, and tutelary dentistry ''.
In one of the pieces in Margaret Atwood's The Tent, young boys who shoot animals for fun are described as tending to become either warlord henchmen or dentists.
One poem by Shel Silverstein has a dentist going to town on a crocodile, even pulling out a tooth that didn't need to be taken out. He says "What's one crocodile's tooth, more or less?" By the end of the poem, he is eaten in a single bite by the crocodile, and the poem ends asking "What's one dentist, more or less?"
Live Action TV
In Married... with Children, Al's new dentist, after the two have established a rapport, promises to go easy on him while drilling...until a call from his ex-wife's attorney sends him over the edge.
Dr. Oliver Bloom in "Mr. Monk Goes to the Dentist". The episode has Monk get tortured by Dr. Oliver Bloom, who has killed an armored car robber he stole some bearer bonds from, and wants to know whether the guy he plans to fence the bonds to is under police surveillance. Dr. Bloom and his assistant Teri even compare the torture session to the Marathon Man dentist torture.
In Seinfeld, Jerry attends an "adults only" dentist who doesn't allow kids in his office, keeps copies of Penthouse in the lobby, and routinely swaps nurses with his fellow dentists. After waking up from an anaesthesia induced coma, Jerry is under the distinct feeling he's been violated. Later on, his suspicions are confirmed. In another episode, the same dentist inflicts pain on Jerry after finding out Jerry was telling "anti-dentite" jokes (You know what the difference is between a dentist and sadist? Newer magazines.)
Alias has a torturer who removes peoples' teeth (including one of Sydney's), known at Television Without Pity as "The Sadistic Dentist of Asian Persuasion".
Doesn't fit this trope perfectly, but on Desperate Housewives, Orson is a dentist and is certainly "depraved": He helped his mother dispose of a body and attempted to commit vehicular homicide, which later made him lose his license.
Dexter: One of the men from the group of rapists is a dentist. Notable in that Lumen tracked him down, and knew it was him off of a gut feeling.
A Lighter and Softer version appears in the Nickelodeon comedy series Turkey Television, with the dentist making small talk with his patients while handcuffing them to the chair.
A prank on Prank Patrol involved a visit to the dentist where the dentist turned out to be one of these.
In Louie, the titular character visits a dentist that specializes in treating people with odontophobia. After giving him an excessive dose of nitrous oxide and an unspecified pill, Louie has a series of hallucinations ending in the dentist sensually inserting a banana into his mouth. When he suddenly snaps out of the dream state, the dentist is seen hastily zipping up his fly.
On The Golden Girls, Rose is groped by her dentist after a procedure. Uncertain, she declines to complain. But when he tries it again during a return visit, the infuriated woman vows that she will file a report with the state dental board.
A both funny and creepy version on Freaks and Geeks: shortly after seeing his friend Neal's dad out in public with a woman who is not his wife, Sam (who is fourteen) has a dentist appointment. Neal's dad is his dentist. Once he has him in the chair, Dr. Schweiber starts telling him he didn't understand what he saw and asking if he's mentioned it to anybody, and ends up taking about how lonely you get when you're older you get lonely and start to feel you've been missing something in your life… all while Sam lies there froglike with a big plastic thing in his mouth.
Referenced in one verse of the Owl City song "Dental Care".
"Have a seat", he says pleasantly
As he shakes my hand and practically laughs at me
"Open up nice and wide", he says peering in
And with a smirk he says, "Don't have a fit
This'll just pinch a bit", as he tries not to grin
The Far Side had a dentist father keeping a chair in his house's basement so he could give his son an "appointment" as punishment.
In 1995, there was a hulking brute of a man whose gimmick was that of being a depraved dentist called Isaac Yankem, DDS (ironically, Isaac's own teeth looked horrible). It wasn't exactly a roaring success. Fortunately, the man behind the gimmick, Glen Jacobs, would go on to be considerably more popular as "The Big Red Machine" Kane.
Arch Oboler, creator of the vintage radio horror show Lights Out, did a creepy little number called "A Day at the Dentist's". Stephen King discusses it in his book Danse Macabre.
Warhammer Fantasy Roleplay had, in its first edition, an adventure called Enemy Within. The Big Bad was called "Zahnarzt", which is the german word for 'dentist'. Sadly he wasn't one, but the name cannot be anything other than intentional.
Orin Scrivello of Little Shop of Horrors, from whom the page quote is taken. This leather-clad hoodlum literally gets off on torturing patients. In The Movie, he meets his match in masochistic patient Arthur Denton, whom he eventually throws out of his office in disgust. The roles were memorably played by Steve Martin (seen in the picture above, taken from a different scene) and Bill Murray respectively. A great bit is the scene with the Braces of Orthodontic Overkill in the film adaptation, whereupon it is implied that he removed the jaw of a kid.
One of the early levels of BioShock takes you through the medical ward. In addition to some normal doctors, there is also a dental section...
In one of their developer videos, Dead Space's developers said that they based the lights in the Ishimura off of the light that dentists place above their patients, due to the inherent fear they know many people have of it.
Dr. Loboto in Psychonauts is a mad dentist who harvests brains.
Zahin Schmartz (Punny Name and Bilingual Bonus) the dwarven dentist in The Witcher isn't a villain, but takes unabashed pleasure in his patient's pain. When the city is on fire, he comfortably sets up shop in a torture chamber because it already had all the tools he needed. Also collects teeth, and has an academic appreciation for monster teeth.
One of (many) recurring background characters in Sluggy Freelance is Nana Avarre, the "angsty dentist" who combines stalking, Goth, and dentistry into one dangerous package. She likes to work without painkillers, but she still manages to get patients to return because her waiting room has arcade games. She was also one of Riff's old flames. So terrifying is she that when Torg was attempting to sabotage Leo, then a boyfriend of Zoe's, he gave him a coupon for a free cleaning from her office. Which actually went to Kent, whose screams were heard outside the clinic. They're dating now.
Subverted in Johnny Bravo in that the title character's dentist seems to like to torture very much, which causes Johnny to run away and cause havoc in the hospital. Then after he gets captured, the dentist works very efficiently and cures Johnny in seconds.
Hermey from Rudolph the Red-Nosed Reindeer is a subversion. He is a heroic character, who helps in the defeat, or in other words, the Bumble becoming a good guy.
Variant: In Codename: Kids Next Door, the villain Nightbrace acts as an evil dentist. His secret identity, however, he is a sweetshop owner who was expelled form dental college after trying to put braces on babies. (The greatest irony is, in his first appearance, he is defeated because a licensed dentist helps the heroes.)
Subverted in an episode of Justice Friends, when Krunk has a piece of potato chip lodged in his tooth and Major Glory refuses to let him go see a dentist. After watching Krunk be subjected to various unpleasant and unsuccessful methods to correct the problem, Valhallen simply takes him to the dentist, where the chip is removed painlessly in a few seconds. Played straight when Major Glory is forced to go to the dentist himself at the end of the episode, but only because he refused to go to regular check ups and thus had lots of cavities.
Metalocalypse plays with this trope, with Nathan fearing that his dentist will try to kill him. He eventually gets over it, and instead manages to befriend him instead, realizing that he actually does need a friend. He still kills himself after the credits roll when out hunting with Nathan later, after commenting on how he appreciates their friendship.
On Cow and Chicken, the Devil is some kind of self-appointed orthodontic policeman who fits the entire town into painful, elaborate braces and headgear.
In Storm Hawks, its implied that all Wallop dentists are like this.
Doug had an episode where Doug had a cavity, which featured him and Skeeter going to see a Smash Adams film where Smash fights an evil dentist named Dr. Decay, a spoof of Dr. Szell from Marathon Man (right down to going "Is it safe?"). After Doug gets a cavity, he sees the name of the dentist he is going to see is "Dr. D. Kay," and imagines they'll be a sadistic loony like the one in the movie. Instead, Dr. Kay turns out to be a kindly woman who painlessly fixes Doug's cavity.
In Dan Vs. "The Dentist", Dan's dentist seems overly friendly at first, but is later revealed to be a sadistic supervillain who deliberately damages his patients' — who are children — teeth, forcing their parents to make repeated and expensive visits. He also plans to implant pain-inducing mind control devices into the teeth of world leaders so he can rule the world. It doesn't help that the dentist is voiced by Mark Hamill, who also voiced the Joker, who as mentioned above invoked this trope as well.
One Goof Troop family album episode featured Prehistoric Goofy putting Prehistoric Pete through a great deal of abuse in various failed attempts to pull a bad tooth so Pete wouldn't have to go to the dentist. In the end, Pete ends up at the dentist by accident, and he removes the tooth painlessly. The horrific drill-like thing that so terrified Pete was actually a watering can used on the dentist's potted plants.