Monk has stiff competition solving the case of a murdered jewelry store owner from a second-rate PI with a loser reputation who suddenly displays skills even more amazing than Monk's.

On Halloween, Monk visits his brother Ambrose in his childhood home to await a visit from his long-absent father, but things take a strange turn when a masked trick-or-treater repeatedly tries to steal Halloween candy from Ambrose's house.

When Natalie finally catches up with the pizza guy who mistakenly left her $50 in change, she finds him dead in his car. She feels compelled to solve the murder but Monk, sick in bed, offers little help.

Monk goes undercover as an office worker and revels in the office routines and actually starts making friends and a possible romance as he tries to solve a murder that occurred in a parking garage next to the office building as well as who injured the hand of the man who hired him whose hand was slammed into a car door probably by the murderer. But Monk's new found popularity may come to a screeching halt if he won't put on the pair of rental (previously used by other people) bowling shoes for the showdown match between his office team and their rival team.

While on vacation for his anniversary, Mr. Monk chats with an intrusive but well-intentioned man at dinner. But when he wakes up the next day, everyone insists that the man was never there.

For the first time in years, Monk has made progress in therapy. But when Natalie discovers that Trudy may be alive, she risks unraveling her boss completely.

Natalie asks Randy to be her date to her brother's wedding. But when he's run down in the parking lot, Monk steps in to figure out what exactly is going on.

Monk encounters an old crush from junior high when she hires him to discover why her housekeeper was killed and her favorite painting vandalized.

The department flies into action after one of their own is poisoned by a secret Santa gift at their very own Christmas party.

Monk investigates the death of a model after his favorite shirt inspector's son is accused of the crime.

After a vicious truck stop attack, Monk awakens with amnesia in a desert hamlet, married to a domineering loon, and suspicious of the circumstances surrounding the hasty departure of a waitress.

While investigating a murder, Stottlemeyer gets into an argument with a cop at the scene who snidely tells him he has been seeing his wife. As a result the crime scene was deemed contaminated. He later asks Monk to follow his wife to see if it's true.

Adrian is one of four detectives on the hunt for a priceless diamond that promises a handsome reward for its finder.

Despite everyone's disbelief that a hero making the news is actually a coldblooded killer, Adrian tries to prove that a celebrity astronaut is responsible, despite an airtight alibi.

Monk must face his fears of dentists after Randy believes he witnesses a murder while under anasthetics. The problem is, the case is connected to a recent armored car robbery.

Lt. Disher and Captain Stottlemeyer capture a "Most Wanted", Colombian criminal, Miguel Escobar, who's wanted for drug trafficking crimes in multiple states, and arrest him for a local homicide. Escobar is notorious for escaping custody, so Stottlemeyer must take extra precautions to ensure that this does not happen while Escobar is in his custody. Captain Stottlemeyer learns that the US Attorney General is ordering him to turn over Escobar to the Federal Government, and is to do nothing more than detain their prisoner until the hand-off, following an extradition hearing. This takes place in the same courthouse where, much to his dismay, Mr. Monk is unable to talk his way out of jury duty, and finds himself forced to hear the case of a robbery/stabbing of a man out to make a bank deposit. During the course of deliberating the robbery case, however, Monk is inadvertently pulled into the Escobar saga.