Monk is committed to an asylum, where he becomes convinced the chief psychiatrist committed a murder several years prior.

Renowned philanthropist Henry Rutherford is killed when a minor earthquake rocks the city and sends a display case falling on top of him. But when Monk examines the scene, he finds clues that suggest foul play.

When monk's favorite singer, Willie Nelson, is suspected of murdering his tour manager, Monk steps in to clear his name.

Sharona's actress sister, Gail, is suspected of murdering Hal Duncan, a fellow actor who dies onstage after Gail stabs him with what she insists is a retractable knife. When Sharona's mother (who thinks that Sharona is Monk's partner, not his assistant) arrives for a visit and Sharona tells her the bad news, Monk and Sharona promise to ""do whatever it takes"" to discover what really happened. ""Whatever it takes"" turns out to be a bit more than Monk bargained for, however. After talking with the props manager, he begins to suspect that Jenna Ryan, Gail's understudy, somehow killed Duncan and framed Gail, even though she was at a party on the other side of town when Duncan died. In order to talk with and observe Jenna, he endures a painful half hour at a speed dating service and even agrees to take the dead man's part in the play for two days until a new actor arrives. While Monk is on stage battling stage fright and fully aware that one of the knives on the stage is real, Sharona searche

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,

After visiting the set of the hit TV series Crime Lab S.F. during a celebration of its one hundredth episode, Monk suspects the show's star, Brad Terry, of murdering his ex-wife so he won't have to share his huge new paychecks with her. But the actor's alibi seems solid--he was with photographers when the victim's screams were heard. To complicate matters, a fan confesses to the crime and Terry passes a lie detector test. After Terry invites the captain, Disher, and Sharona--but not Monk--to a party, Monk realizes that Terry reminds him of a popular boy who treated him the same way in sixth grade and begins to doubt his own instincts. But when Stottlemeyer invites Monk to hear Marci's confession, Monk's doubts shift to Marci's story. When she tells him that Terry's ex-wife was once an actress who made a single B movie, Monk has the clue he needs to solve the crime.

Captain Stottlemeyer and Lieutenant Disher are making a routine arrest when a mysterious man in a car drives up and shoots at them, wounding Stottlemeyer. When Monk and Disher try to apprehend their prime suspect, Monk’s obsessive-compulsive disorder allows the suspect to escape. Consumed with guilt, Monk goes to Dr. Kroger who gives him a drug to alleviate his obsessive-compulsiveness but impairs his sleuthing ability.

When Monk, Natalie, and Julie get stuck in a traffic jam after a multi-car collision blocks the freeway, Monk gets out of the car to investigate. He soon deduces from the absence of skid marks and other clues that the young man in the overturned Volkswagen that caused the pile-up was murdered and his body placed in the car to make his death look like an accident. But the highway patrolman in charge of the ""accident"" scene wants nothing to do with Monk (or the not-very-successful lawyer who has latched onto him), and the mountains blocking the signal prevent Monk from calling Captain Stottlemeyer for an authorization to investigate. Monk briefly returns to Natalie's car, where he finds Julie in need of a bathroom and Natalie nursing an injured wrist. Unfortunately for them, Monk's mind is on the fatality, and he returns to the Volkswagen. The angry officer gives him the victim's name and occupation (environmental activist), but he still refuses to listen to Monk's evidence. Meanwhile, t

After twenty-two-month-old Tommy Graser finds a severed finger and gives it to a policeman, Monk walks through the park with Tommy trying to retrace the child's steps. He finds no body or other incriminating evidence, but he does discover a surprising affection for the placid and intelligent toddler, who constantly repeats Monk's name and quietly submits to having his hands wiped when he touches ""nature."" A lab technician identifies the finger as that of a twenty-five-year-old man, and Monk deduces from a callus that the young man played the violin. After visiting the home of Daniel Carlyle, a musician who fits this description, Monk concludes that Daniel's mother and her other son, Jason, killed Daniel and that Jason is masquerading as his brother. Meanwhile, little Tommy is temporarily removed from the custody of his foster parents, and Monk surprises everyone, including himself, by volunteering to care for him for two weeks until his new adoptive parents can take him. With Tommy in

Monk is reunited with his agoraphobic brother, Ambrose, after the murder of an armored car driver.

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.

When Natalie convinces Monk to go into business as a private eye, his first case is a seemingly innocuous fender bender that leads to a far more dangerous investigation.

When Monk's truck driving father rolls into town at Christmastime, Monk joins him on the road, where they stumble across a very peculiar mystery.

Monk is arrested for murder, and finds that he has to go on the lam to clear himself.

As Monk and his friends watch a TV news magazine piece on the solution of his hundredth case, he realizes that one of the victims was murdered by a different killer.

Monk becomes involved in the disappearance of a city official that could have ramifications concerning Trudy's murder.