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 three mornings later 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.

A judge is murdered while placing a 911 call, but before she dies she names her attacker - notorious criminal Dale Biederbeck. The problem is, "Dale the Whale" is over 800 pounds and hasn't left his bed in years.

A police officer and friend of Stottlemeyer is framed for a crime he didn't commit involving a ferris wheel. Meanwhile Monk tries to convince Stottlemeyer to get him reinstated.

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

When billionaire software magnate Sidney Teal is shot dead by ex-cop Archie Modine after allegedly turning mugger and another policeman mysteriously flees the scene, Stottlemeyer calls in Monk to investigate. Not only is the idea of a billionaire turning mugger hard to swallow, the circumstances of the mugging are suspicious. Why, for example, would a mugger wear knee and elbow pads? Meanwhile, Sharona threatens to quit (this time for sure) when her paycheck bounces, and Stottlemeyer is hounded by reporters demanding information on "Fraidy Cop." Unable to continue the investigation without Sharona's help, Monk returns to the seemingly unsolvable mystery of his wife's murder only to find that his "new" clue isn't new; he's already talked to writer Kelly Street three times. Sharona finds that selling lamps isn't nearly as much fun as working for Monk (with or without money) and comes to the rescue with a new clue involving Teal and Modine.

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.

A woman is murdered during the San Francisco marathon and Monk suspects her married lover. But he was running the race, and his tracking chip says he never left.

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.

Renowned philanthropist Henry Rutherford is killed when a moderate 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.

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