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 listening to Trudy's last message, Monk finally discovers who killed his wife. Racing against time before he dies of poison, he must make a fateful decision.

Monk suspects that the man responsible for the mail bombing murder of rich and beautiful Amanda Babbage is the victim's brother, Brian – who has been in a coma for four months after attempting to lure Stottlemeyer and Disher into a car chase and crashing into two cars. Since the package was postmarked three days before the bombing, Stottlemeyer is naturally skeptical, but he prefers siding with Monk to tagging along behind Agent Grooms of the Bureau of Alcohol, Tobacco, and Firearms, who suspects the victim's other brother, Ricky.

Who would murder a death-row inmate forty-five minutes before his execution--and why? That's the question Captain Stottlemeyer asks Monk--but Monk's response is to ask why it matters. As Monk is hurrying to leave the prison, however, he gets a phone call from his old nemesis, Dale ""the Whale"" Biederbeck, that changes his plans. The police consider Dale a suspect in the inmate's murder (the young man owed him twelve hundred dollars) and refuse to give him a window in his cell until his name is cleared, so Dale strikes a bargain with Monk--solve the case and he'll provide information about Trudy's murder. After interviewing the cook who prepared the dead inmate's last meal, Monk notices that another cook never clocked out the evening before. The missing cook is found dead in a freezer with a wad of bills in his apron pocket--clearly the person who bribed him to poison the inmate was afraid he would talk and killed him, too. On his way out of the prison, he receives another phone call, th

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.

On her way to film a documentary (apparently about a union dispute), Captain Stottlemeyer's wife, Karen, is badly injured when her car is struck by a tow truck whose nonunion driver has been killed by a sniper. Distraught and furious, the captain blames a sleazy union official and his thug, a theory that seems to be confirmed when a second tow truck driver is murdered. But Lieutenant Disher, in charge of the crime scene investigation, discovers an odd detail that doesn't fit well with this scenario – both the assailant and the murdered truck driver were barefoot. Empathizing with the captain's anguish, Monk offers to do whatever he can to help and of course ends up investigating the case. A small dog that follows Sharona from the crime scene leads her to the home of a handsome man who seems attracted to her, but Monk is more interested in the next-door neighbor's off-kilter sundial. Meanwhile, the captain, fearing that his wife will die, becomes increasingly violent, taking out his anger...

When English teacher Beth Landow falls from the clock tower at Trudy's former high school, the assistant principal doubts the police department's conclusion that the death was a suicide and invites Monk to investigate. Monk quickly concludes that the suicide note is a forgery: a highly respected English teacher wouldn't confuse ""its"" with ""it's."" A few words with the teachers in the lounge lead him to suspect that the murderer is a science teacher, Derek Philby. Unfortunately for Monk, Philby was proctoring an SAT exam when Ms. Landow's body landed on Philby's car, setting off his car alarm and alerting the entire school to her death. Armed with a strong suspicion but no evidence, Monk becomes a substitute teacher in hopes of finding the information that will incriminate Philby, who arrogantly informs him that he's ""failing the class""--he has no evidence to support his hypothesis. Faced with students who throw erasers at him, an irate father who is also the school's gym teacher threat

When a friend's college-age son dies mysteriously in Mexico, the mayor sends Monk to investigate. Doubting the coroner's report that the young man ""drowned"" in mid-air, Monk nevertheless has difficulty concentrating on the case. His eighteen suitcases carrying not only his clothes and ""back-up pillowcases"" but a year's supply of food and his favorite brand of bottled water are stolen, leaving him with nothing he considers safe to eat or drink. Even worse, someone is trying to kill him, first by running him down with a pick-up truck and then by planting an explosive device behind a picture that he compulsively straightens every time he enters his room. Neither the witnesses nor the police, a south-of-the-border caricature of Stottlemeyer and Disher, offer any helpful leads--except for the mention of another unsolved murder, this one a mauling by a ""wild lion,"" the previous year. The fact that both victims were from San Francisco offers Monk the clue that he needs to solve the case and e

Captain Stottlemeyer must take a page from the Book of Monk when his wife nags him into looking into the murder of the world's oldest man. First on-screen appearance of Karen Stottlemeyer (Glenne Headly).

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

After a phone call from Lt. Disher, Monk and Sharona find him in Captain Stottlemeyer's office, drinking Scotch to console himself because his 58-year-old mother has married a 37-year-old antique dealer he's sure is up to no good. The con man, Dalton Padron, has taken his aging bride to a marriage counseling clinic for their honeymoon, and Sharona persuades Monk that the best way to catch him is to pose as husband and wife and join him at the clinic. In a group therapy session, Sharona accuses Padron of winking at her and, in the scuffle that follows, snatches an old letter from his jacket pocket. The letter confirms their suspicions: Padron is after the gold that was stashed away 150 years earlier by the crazy old prospector who once owned the house. Padron later grabs the letter and burns it, but not before Monk and Sharona discover that the secret is somewhere in the hundreds of journals that the old man wrote before he died. Early the next morning, Sharona follows Padron into an ol

Faced with a string of nine brutal murders, all with different MOs and no apparent similarities among the victims, Captain Stottlemeyer calls in Monk to help him investigate. Suspicion falls at first on Henry Smalls, an insurance agent whose calendars appear in three of the victims' photographs. But as Monk, accompanied by Sharona and her new boyfriend, Deputy Mayor Kenny Shale, waits in the dark for Smalls to return home, he helplessly witnesses a fatal stabbing in which the suspect becomes the victim. Rushing after the murderer, who is wearing a ski mask, Monk tries futilely to subdue him, but all he's able to discover is that the murderer bites his fingernails. As the number of victims rises to eleven, the diversity of the victims, combined with the fact that they all live in Marin County, suddenly causes both Monk and Stottlemeyer to realize that they're all members of a jury. The ensuing investigation leads them to a six-year-old personal injury case, won by the plaintiff, who is

When Monk's paperboy is murdered on his doorstep by a guy looking to steal his newspapers, Monk turns to the pages of the newspaper for clues to solve the baffling crime.

When Sharona returns to San Francisco to handle legal issues related to an uncle's death, Monk suspects foul play and is torn between the differing styles of Sharona and Natalie.

Monk's first flight proves to be harder than he anticipated when he begins to suspect that a fellow passenger murdered his wife.

Monk and the police have a killer right where they want him... until the case goes to court and a hotshot lawyer demolishes the prosecution as he uses Monk's phobias against them

Upon being reinstated, Monk is put in charge of tracking down a serial killer.

A former San Francisco police detective suffering from an extreme case of obsessive-compulsive disorder is called in to investigate an apparent assassination attempt of a mayoral candidate in which one of his bodyguards is killed.

When a woman drives off the road to her death, her body is mysteriously found the next morning by a psychic known for fudging the truth. Monk must discover if she's telling the truth this time, or else let a murderer go free.

While on vacation at a resort, Benjy claims he witnessed a murder. Monk believes him, but with no body and the cleanest crime scene Monk has ever seen, it's going to be hard to convince everybody else.

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.

Monk reluctantly adopts a dog while looking into the suspicious disappearance of its owner.

A very tidy woman who resembles Trudy turns Monk's head while he's investigating a triple homicide. The only problem is, she's the prime suspect.

When a ruthless CEO and his wife are lured to an industrial park and are shot dead in their car, Monk connects their murders to a star baseball player's quest for the single season home run record.

When a sarcastic and unpopular ringmaster is murdered by an acrobat wearing a face mask and a Ninja-like costume, Stottlemeyer suspects an animal trainer who not only has a motive but also owns the murder weapon. Monk, however, suspects the ringmaster's ex-wife, a trapeze artist billed as The Queen of the Sky who is also a sharpshooter. Meanwhile, the Monk alienates Sharona by telling her that her fear of elephants is irrational and advising her to suck it up.