Randy suffering from a toothache leads Monk into one of the most personally horrifying cases of his career when the young officer claims he saw the dentist and his hygienist murder a man while partially sedated.
This episode includes examples of the following tropes:
- 10-Minute Retirement: Randy quits the force in the middle of the episode because very few people were taking his claims seriously. By the ending, he returns with a warm reception.
- Ain't Too Proud to Beg:
- Monk begs for the dentist to wash his hands before extracting his teeth. Bloom agrees finally to get Monk to stop screaming.
- Stottlemeyer asks for Randy to return to work. He says that he needs his right-hand man to help him solve cases.
- Anything but That!: When about to be tortured by the dentist and his assistant, what freaks Monk out the most, and the one thing he begs the dentist not to do, isn't the painful tooth extraction. It's the dentist performing the operation without washing his hands beforehand. Monk puts up such a fuss that the dentist actually gives in on this point and agrees to wash his hands.
- Asshole Victim: Denny Jardeen was a former cop who killed two armored car guards, so it isn't the worst thing that he gets murdered.
- Berserk Button: Randy becomes furious enough to quit the force after not being taken seriously when he witnesses the murder.
- Baddie Flattery: Dr. Bloom notes that Monk takes good care of his teeth, while preparing to torture him.
- Big Damn Heroes: Thanks to Randy realizing that what he heard under sedation was "bearer bonds" and not "Barry Bonds," he, Natalie, and Stottlemyer arrive just in time when the dentist and his hygenist were about to pry out Monk's teeth.
- Bludgeoned to Death: The man Randy sees getting murdered is killed from Terri hitting him with a large tooth decoration.
- Bound and Gagged: An interesting variation; Monk is strapped to a dentist's chair, and his mouth is forced open that leaves his speech garbled.
- Cassandra Truth: During the dental procedure for a legitimate toothache, and while being placed in novocaine, Randy ends up witnessing a brutal confrontation between the dentists and a bald man demanding "Barry Bonds" and saying that "he was worth $13 million," and tries to report it to his co-workers, only to be laughed at and/or met with disbelief (the fact that he was doped up on novocaine when it was happening did not help matters much), eventually being fed up at not being believed and quitting the force. It later turned out that Randy was actually quite correct in what he saw (and what he really saw was one of the armored car robbers confronting and being killed by the dentists because they found out about the robbery proceeds and ripped him off).
- Chekhov's Gun:
- As Dr. Bloom begins to operate on Randy, he mentions that he can easily identify cops and guess their ranks because he's on a lot of cops' insurance plans. Once Jardeen is identified, Monk realizes that he went to Dr. Bloom because he was the dentist covered by Jardeen's insurance.
- Dr. Bloom says that people see and say all sorts of things when they're under sedation. It turns out that Jardeen spilled the whole story about the robbery and the bearer bonds while in the dentist's chair.
- Cold-Blooded Torture: Zigzagged. Dr. Bloom doesn't actually hurt Monk while torturing him, not for lack of trying. Instead, the dentist gives him a checkup, weaponizing Monk's dentist phobia against him. Monk is prepared to spill everything, but Bloom is about to drill one of his teeth anyway to make sure the info is accurate.
- Continuity Nod: Randy puts his band "The Randy Disher Project" back together, which was alluded to during "Mr. Monk and the Secret Santa".
- The Dentist Episode: Monk visits Randy's dentist himself as part of his investigation, and flashbacks to Randy's appointment are shown as well.
- Depraved Dentist: Dr. Oliver Bloom and his assistant Terri. They're not actually depraved prior to the events of the episode, until Jardeen comes to them to get his tooth fixed because he broke it during a fight with one of the guards during the hijacking. While under anesthesia, he divulges the details to them without his knowledge. Dr. Bloom and Terri, rather than calling the police, get greedy and steal the loot from Jardeen's house. When Jardeen finds out, he confronts them while they are operating on Randy for a toothache, and Terri strikes Jardeen multiple times with a giant plastic tooth, then they dispose of the body. Intending to now fence the stolen bonds, they kidnap Monk and torture him with a dental drill, intending to figure out whether the fence they want to sell to is under police surveillance. Not only is the scene similar to Dr. Szell's torture conducted in Marathon Man, but Dr. Bloom and Terri outright compare it to that.
- Driving into a Truck: The robbers hijack the armored car by having a garbage truck shove it into the back trailer of an eighteen wheeler.
- The Diss Track: Randy's song "I Don't Need a Badge" consists mostly of jabs against "the man", the police, and Stottlemeyer (though he never uses the name, it's obvious who he's referring to when he says "I don't need your mustache, don't you condescend to me"). Understandably, Stottlemeyer doesn't like it much.
- "Eureka!" Moment: Randy realizes that the dentists were talking about bearer bonds and not the baseball player Barry Bonds when he sees a newspaper article about the heist.
- Fatal Family Photo: A variant; one of the armored car guards talks about how he and his fiancée are seeing the wedding planner that evening. Both of them die during the holdup.
- Foreshadowing: Stottlemeyer figures quickly that Randy isn't going to the dentist because he doesn't want to dip into his sick days.
- Gaslighting: Dr. Bloom and Terri try to convince Randy the murder he witnessed was a hallucination while under anesthesia. Randy's friends also say it, but in their case, they sincerely think so; they aren't intentionally trying to gaslight him (and they eventually believe him).
- Idiot Ball: Upon finding out they ripped him off, Jardeen decides to confront Dr. Bloom and Terri while they are attending to a patient who is a cop. Even though Randy is sedated, he heard enough to figure out there was something fishy.
- Improvised Weapon: How many murders can you think of where the murder weapon was a giant tooth?
- Interrogated for Nothing: Believing that the buyer for the bearer bonds is being monitored by police, Dr. Bloom and Terri torture Monk for information. Unfortunately, Monk has no idea about what they are asking, so all they end up doing is incriminate themselves while exacerbating Monk's already crippling fear of dentists.
- Mugging the Monster: Ex-cop Denny Jardeen and his friends rob an armored car. In the fight, one guard manages to punch Jardeen, breaking one of his teeth, before he is shot dead. Jardeen goes to his dentist to get his tooth repaired, but under anesthesia, he divulges everything about the robbery to Dr. Bloom without knowing it. Instead of going to the police, Dr. Bloom and Terri go to where the loot is being stored and steal it. But Jardeen figures it out, and a few nights later, when Dr. Bloom and Terri are operating on Randy for a toothache, Jardeen barges in confronting them, and they kill him in a fight.
- One Dialogue, Two Conversations: Randy, suffering a toothache, steps away from the crime scene for a bit to weep and moan from the pain privately. Natalie, who's heard that one of the dead guards was engaged, thinks he's upset about the senselessness of it all and encourages him that It's Okay to Cry. Even when he mentions his tooth, she doesn't get it, because she'd been talking about them coming up with an excuse to save Randy's pride over his sensitivity. When Stottlemeyer tells her Randy's been complaining about the tooth for days, she slaps Randy for "lying to her." Randy protests that he tried to tell her.
- Playing Sick: Stottlemeyer implies the reason Randy doesn't want to go to the dentist in spite of a genuine toothache is that he wants to save his sick days on days where he isn't actually sick. He isn't wrong, either.
- Properly Paranoid: Monk has a crippling fear of dentists due to a bad experience, a fear so severe, in fact, that he is completely unwilling to go beyond the waiting room while Randy and Natalie investigate the room where the murder took place, and later has to be pried off when he's literally frozen in fear in his seat during the wait (presumably from hearing a drill whirring in the background). Turns out he is very much justified in this fear, as he ends up being abducted and then tortured by the same dentists about potential clients for the bearer bonds and whether the police had them monitored (an incident that also results in his fear of them being heightened as a result to the extent that he refuses to go to a dentist even after one of his teeth gets chipped).
- Rage Quit: Randy angrily leaves the police force because no one would believe him about Dr. Bloom, and the fact that other officers make fun of him because of it.
- Shout-Out:
- When telling tales about what they dream of under anesthesia, Detective Patterson says that he dreamt he was the Green Lantern.
- Dr. Bloom and Terri decide that they'll torture Monk in a manner very similar to the infamous torture scene in Marathon Man. Terri even lampshades it by saying Monk is going to live through it.
- Stylistic Suck: Most of Randy's music, but especially the hilariously slipshod, badly animated music video he presents to the others at the end. It cannot be described, only witnessed...
- Villain Ball: Even after taking the allegation semi-seriously and investigating Dr. Bloom on Randy's behalf, neither Stottlemeyer nor even Monk find any reason to suspect him of anything...until Bloom and Terri decide to kidnap Monk, obviously incriminating themselves the moment his friends come looking for him. They justify it as needing to figure out if their buyer is being watched. When Monk tries to tell them what he thinks they want so they'll release him, they try to torture him further.
- Working the Same Case: Randy's account of witnessing Dr. Bloom and Terri kill a man is connected to the armored car robbery. The man was one of the hijackers, who visited Dr. Bloom after one of the guards knocked out his tooth and talked about the stolen bearer bonds while under anesthesia.
