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Just 45 minutes away from his scheduled execution, death row inmate Ray Kaspo dies in his cell from a poisoned last meal. Monk is brought in to investigate, but turns down the case -- until he receives a call from his old nemesis, Dale "The Whale" Biederbeck (Tim Curry), who is locked up in the same prison as the murdered Kaspo. It seems that Dale is a prime suspect in the murder, and he needs Monk to find the real killer in order to get the authorities off his back. In exchange for Monk's help, Dale promises to provide information relating to the death of Monk's wife, Trudy.
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160
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San Francisco antique dealer Raymond Toliver reads aloud from an old, yellowing confession written by 19th century prospector Joshua Skinner. It describes how Skinner murdered his mining partner Gully Watson during the gold rush of 1849, built an enormous house on the site of the gold strike, then hid Watson's share of the mother lode -- a cache worth millions that has never been found to this day. "Where is the gold?" Stemple's letter asks. "The answer is in my journals." As Toliver ponders aloud how anyone could murder their partner for a cache of gold, his own partner, Dalton Padron, bludgeons him to death with a sewing machine. A few days later, Monk is entreated by a very drunk Lieutenant Disher to look into the whirlwind nuptials of his unglamorous, 50-something mother, Maria, to a dark, mysterious and much younger antique dealer named Dalton Padron -- whom Disher doesn't trust.
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160
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After a sniper's bullet kills a tow truck driver, the truck careens into Karen Stottlemeyer's car as she is making her way to work, sending her to the hospital. As Captain Stottlemeyer grapples with the possibility of losing his wife, Lieutenant Disher speculates that an ongoing local union dispute may be behind the shooting. Eager to find the person responsible for nearly killing his wife, Stottlemeyer confronts union leader Harry Bolston at a union rally. Bolston denies any wrongdoing, and Monk believes him, suspecting something just isn't right. But Stottlemeyer's clouded judgment has made him obsessed with nailing Bolston and the union.
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160
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An elderly woman is strapped to her chair and kidnapped from her home by two masked intruders who leave a spray-painted lightning bolt on her wall. Captain Stottlemeyer and Lieutenant Disher immediately suspect a 1970's radical group, the Lightning Brigade. Dissatisfied with the police investigation, the victim's granddaughter, Julie Parlo (Rachel Dratch), asks for Monk's help. In exchange, Julie, a law student, promises to get Monk reinstated to the police force with a clever legal strategy. Eager to get back on the force, Monk agrees to help.
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160
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Monk and Sharona are called to the home of Susan Molloy, the ex-wife of popular TV star Brad Terry. Once there, they learn that Susan was stabbed inside the house while Brad was out front dealing with the paparazzi -- that is, until everyone heard Susan's screams. The evidence points to a break in, but Monk thinks otherwise. Monk and Sharona pay a visit to the set of Brad's hit TV show, "Crime Lab S.F." There, they learn that the show is celebrating its 100th episode, which in turn means a VERY big payday for Brad -- a payday he's likely unwilling to share with his ex. Monk thinks he's got him, but when the TV star volunteers for a lie detector test and passes with flying colors, it's Monk who's been had.
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160
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An elderly woman wins a cherry pie at a town raffle. Before she can drive home with her prize, a man approaches, demanding she give him the pie. She refuses, so the man kills her and drives away with her body. Captain Stottlemeyer and Lieutenant Disher consider the case a routine carjacking, but Monk suspects there may be more to it. However, before Monk can get too involved, he gets a surprising phone call from his brother Ambrose (John Turturro), who wants to discuss a matter of "life or death." The brothers haven't spoken in seven years, ever since Ambrose failed to contact Monk after the death of Monk's wife Trudy.
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160
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After Nestor and Jose Alverez deliver the morning paper to their most demanding customer, Adrian Monk, they notice someone trying to steal it. While trying to stop the thief, Nestor is pushed to his death. Monk's apartment is soon turned into a hub of disorder and distractions as the police search the crime scene. Monk's nerdy neighbor Kevin stops by to check out the commotion, and also introduces his hot new girlfriend, Vicki. With no crime scene clues and no obvious suspects or motive, Monk is convinced that there must be something in the newspaper that the killer did not want him to see
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A tollbooth operator is killed at work. Across town, a woman is killed in a movie theatre. Those are just two more victims the police have added to the growing number of bizarre homicides that have been sweeping the city in recent weeks. Immediately, Monk is suspicious of the details surrounding both murders and by the clues -- or lack thereof -- left at the various crime scenes.
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160
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Elliot D'Souza, Chief Financial Officer for a high-powered publishing company, is working out in his private gym alone when suddenly the weight of his barbell overwhelms him and it comes crashing down violently on his throat. He's killed instantly, choked to death by his own workout equipment. Is it just an unusual accident, or something more sinister? Elliot's secretary, Miss Luden, is certain that Dexter Larsen (Gary Cole), the infamous publisher of the gentlemen's magazine Sapphire, somehow orchestrated her boss' death. As it turns out, Elliot was planning to close the doors of the infamous swinging party palace, the Sapphire Mansion. Not satisfied by the results of the police investigation, Miss Luden asks Monk and Sharona to take the case.
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It's a quiet afternoon in the San Francisco suburbs. Amanda Babbage chats on the phone as she retrieves her mail, confiding to her friend a recent series of difficulties between her and her brothers. Little does Amanda know that the package she's just carried into the house is in fact a bomb. This oversight is made clear a few moments later when, as she attempts to open the package, it explodes, killing her instantly. Though Monk is in the middle of a personal crisis -- his psychiatrist, Dr. Kroger, has left town for vacation, leaving Monk to deal with his obsessive compulsions on his own -- Captain Stottlemeyer nevertheless brings him in to consult on the bombing.
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