In an attempt to stabilize his shaky marriage, Captain Stottlemeyer redecorates his office with the New Age artifacts that his ""hippie wife,"" Karen, has given him, but he can't bring himself to watch the documentary that she spent forty-five thousand dollars to film. When Karen thinks that her documentary subject--the world's oldest man--was murdered, the captain rejects the suggestion as absurd but calls in Monk to pacify her. Unfortunately for the captain, Monk agrees with Karen, and Stottlemeyer finds himself on Monk's front porch with two packed suitcases. Monk, glad for a chance to repay the captain for helping him through his three-and-a-half year ""slump,"" invites him to stay as long as he needs to. Predictably, they both end up with frazzled nerves and very little sleep. Depressed over his own ""slump"" and his inability to solve a five-year-old case involving the death of a seventeen-year-old boy, the captain becomes even more despondent when Monk finds a clue that he missed in

When Monk's older brother Ambrose calls him about a ""life-or-death matter,"" Monk accepts the call grudgingly and agrees to meet the brother from whom he's been estranged since Ambrose refused to attend Trudy's funeral seven years before. In fact, Ambrose, an agoraphobic packrat whose house is full of bundled up newspapers, has not left the home he and Adrian grew up in for thirty-two years. Believing Ambrose's claim that his next-door neighbor, Pat Van Ranken, has murdered his wife after a loud argument, Monk and Sharona visit Van Ranken and decide to follow him. Van Ranken, meanwhile, is behaving very strangely, entering a potato sack race and a bingo tournament in which the prizes include a cherry pie. It's not hard for the Monk brothers to tie Van Ranken to another murder involving a cherry pie--the challenge is finding a motive for Van Ranken and proving that he did it. The episode provides a glimpse of Monk's family background and the reasons for his estrangement from his brother,

Three deaths during a city-wide blackout result in a joint investigation by Stottlemeyer, Monk, Sharona, and Disher, with the unprecedented cooperation of the FBI and the help of power company spokeswoman Michelle Rivas, an attractive brunette who is inexplicably attracted to Monk. While Sharona and Dr. Kroger pressure Monk to call Michelle, Disher follows up on Monk's suggestion that the power outage is connected to a '90s radical named Winston Brenner. Everything fits--the handwriting in the note, the phrasing, even a pair of photographs. Everything except one small detail at the end of the report--Brenner died in 1995. When the FBI acknowledges the possibility that Brenner may have faked his own death to avoid a trial, Captain Stottlemeyer presents a tree-hugging former friend of Brenner's with the evidence that Brenner is still alive and reminds him that this particular power outage is also a homicide. When the tree-hugger is murdered, it becomes clear that the killer is indeed Bre

With Sharona in New Jersey to visit her ailing mother, Monk is left in the very incompetent hands of his annoying upstairs neighbor, Kevin Dorfman, but the prospect of a week with Kevin is eased somewhat by a visit from Trudy's father, Dwight Ellison. Dwight invites Monk (and Kevin) to spend the week with him and his wife, Marcia – and at the same time investigate gameshow host Roddy Lankman, who appears to be involved in a conspiracy to allow one of his contestants, Val Birch, to win every game. Despite the memories of Trudy aroused by spending time with her parents in her former home and the questionable help of Kevin, Monk discovers evidence that Lankman visited Birch's house – and that Birch visited the site of the accident that killed Lankman's assistant, Lizzie Talvo. To discover exactly how Lankman and his crooked contestant are communicating – and possibly prove that they're involved in something much worse than cheating – Monk becomes a contestant on the game show. His knowledge o

In the middle of the night, Monk receives a phone call from a drunken Stottlemeyer, who has gone to Las Vegas with Disher for a fellow officer's bachelor party. Stottlemeyer believes that a wealthy casino owner has murdered his wife, but he needs Monk's help to prove that the death wasn't an accident. Unfortunately, when Monk arrives in Vegas with Natalie the next morning, Stottlemeyer can't remember anything that happened the previous night--including how his pants happened to be thrown out the window. As Monk and Natalie explore the elevator where the woman died, interrogate witnesses, and reenact the death scene (with Monk in the role of victim), Stottlemeyer tries to retrace his steps and deal with Disher, who has become addicted to blackjack and fallen hopelessly deep into debt. When Monk, at Stottlemeyer's insistence, takes Disher's place at the blackjack table to win back his money, he figures out how the murder occurred as he simultaneously places winning bets, but the casino o

Monk goes to a wine-tasting and finds it a bit more than he bargained for.

Low on cash because they haven't had a homicide to investigate in three weeks, Monk and Natalie search for the stolen Alexander Diamond, hoping to win the million-dollar reward. Unfortunately, they have competition in the form of a retired Scotland Yard investigator, a bounty hunter, and a gadget-loving private detective, all of whom want the reward money for themselves. Monk quickly figures out that the heist was an inside job and that one of the robbers was under five feet tall, short enough to hide inside a roll-top desk. He also discovers a clue linking a perpetrator to a transcendental meditation retreat. With their competitors close behind them, Monk and Natalie head for the retreat, where they find the thief, who is unfortunately dead. Meanwhile, Disher is having to interrogate a strange young woman who keeps turning herself in for such ""crimes"" as stealing pens or murdering a hamster. Monk tells Natalie that he's solved the case and they race to the police station with the other detectives following. The only thing left is to find the diamond before their competitors do.

During the investigation of an armored car heist involving the deaths of two drivers and the theft of valuable government bonds, Lt. Disher tries to convince Captain Stottlemeyer that he witnessed a murder while under anesthesia in the dentist's office. When one of the highjackers, Denny Jardeen, is found murdered, Disher insists that Jardeen is the man he saw Dr. Bloom and his assistant kill while he was sedated. Stottlemeyer still thinks that Disher was hallucinating, and Disher angrily leaves the force, deciding to revive his high school rock band, the Randy Disher Project, as an alternate means of earning his living. Meanwhile, the only clue to Jardeen's murder is two pairs of bruises each ten inches apart on the dead man's chest.

Monk attends his college reunion and uncovers a complex murder plot against one of his former classmates.