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Monk receives some bad news: he’s been called for jury duty. Monk loathes the idea of being stuck in a room with 11 other people, but he has no choice when he’s selected as a juror in a minor robbery trial. When time comes for the jury to deliberate, everyone votes “guilty” except for Monk. It’s 11 vs. 1, but Monk is sure that the defendant is innocent. While Monk tries to win over his fellow jurors by picking apart the evidence, he looks out the window of the jury room and begins to suspect that there is a dead body in a garbage dumpster near the courthouse. Monk gets Stottlemeyer and Disher to check it out, and sure enough, there’s a dead woman’s body in the dumpster!
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160
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After an armored car heist, Monk and Natalie arrive on the scene to join Capt. Stottlemeyer and Lt. Disher in the investigation. While Monk picks up clues, Lt. Disher complains of a horrible toothache. Capt. Stottlemeyer insists that Lt. Disher visit a dentist immediately. Disher goes to the office of Dr. Oliver Bloom, and soon finds himself under sedation while Dr. Bloom extracts a tooth. Then, something strange happens: while floating in and out of consciousness, Lt. Disher sees - or thinks he sees - Dr. Bloom and his assistant kill an intruder. But the Captain doesn’t believe him. Nobody does.
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160
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Civilian test pilot Steve Wagner is a national hero, but not everyone admires him. His old flame, Joanne Raphelson, is about to publish a tell-all book that details the abuse she endured during their relationship. Wagner can’t let Joanne’s story get out, so he pays her a visit. He makes her one of his signature drinks, a “Spacewalk,” and adds a little something extra: a powerful dose of barbiturates. When her housekeeper arrives the following week, she finds Joanne hanging from the ceiling with a noose around her neck. Captain Stottlemeyer, Lieutenant Disher, Monk and Natalie go to Joanne’s house to investigate. It appears to be suicide, but the captain and Monk spot some clues that point to murder.
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160
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Monk and Natalie go to police headquarters to ask Captain Stottlemeyer for a raise. While they are there, Lieutenant Disher brings in Warren Landis, a security guard from a local museum, for questioning. The world-famous Alexander diamond has been stolen from the museum, and the police are interrogating all museum employees. When Monk notices some chemical residue on Landis' fingers, Disher arrests the security guard on drug charges. When Natalie hears that there’s a million dollar reward for the diamond, she convinces Monk to use his detective skills to try to find the stolen gem.
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Monk and Natalie join Captain Stottlemeyer at a junkyard to investigate the murder of a small-time drug dealer named Chicklet. While Monk looks around, a cocky young police sergeant named Ryan Sharkey implies that he’s having an affair with the captain’s wife, Karen. Stottlemeyer punches Sharkey in the face, and then leaves in a huff. Karen emphatically denies having the affair. The captain, still suspicious of Karen, asks Monk to follow her and find out whether or not she’s having an affair.
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It’s late, and Monk and Natalie are at a deserted highway rest area. They’re there to meet a man who claims to have information about Trudy’s murder. Monk has brought an envelope of reward money, and he makes Natalie hide so he can meet the man alone. When the man turns out to be a phony, Monk refuses to give him the cash. A struggle ensues. The man clunks Monk over the head, steals the reward money and Monk’s wallet, and dumps Monk’s unconscious body on a flatbed truck. When Natalie reappears, Monk and the man are both gone.
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When Monk starts noticing imperfections in his shirts, he seeks out the woman who inspects them to make sure nothing is wrong. When Monk meets the woman, Maria Ortiz, he learns that something is wrong. Maria’s beloved son, Pedro, is in jail for the murder of a fashion model named Clea Vance, and Maria has been living under great duress ever since. She knows her son isn’t guilty, and Monk agrees to look into the case.
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160
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It’s the annual Christmas party at police headquarters, and everyone is full of holiday cheer. Monk, Natalie, Captain Stottlemeyer, and Lieutenant Disher are all there. When it comes time to exchange Secret Santa presents, Captain Stottlemeyer has a problem: he’s unable to find the gift he bought for his friend, Detective Chasen. At the suggestion of Alice Westergren, another police officer, Captain Stottlemeyer takes a bottle of port that he received from an auto body shop and re-gifts it to Chasen. Detective Chasen drinks the port, collapses and dies. The port was poisoned!
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Monk and Natalie are cleaning Monk's apartment when they get an unexpected knock on the door. It's Sherry Judd, who went to junior high school with Monk. Intruders have murdered her housekeeper and defaced a painting of her grandmother, and she'd like Monk to investigate. Monk had a big crush on Sherry when they were young, and seeing her again unleashes a flood of memories and emotions. Monk agrees to help her.
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When Natalie needs a last-minute date to her brother Jonathan’s wedding, she reluctantly agrees to let Lieutenant Disher accompany her. The wedding is being held at a posh resort, and everything seems to be going fine - until Disher gets run over by a car in the resort’s parking lot. Disher suffers serious injuries and barely survives the horrible incident. Captain Stottlemeyer and Monk show up to investigate, and they quickly determine that the driver of the car, who fled the scene, must be a member of Natalie’s family. But why would one of Natalie’s relatives try to kill Lieutenant Disher?
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