Adrian Monk, a former San Francisco Police Department (SFPD) detective, comes out of forced retirement to investigate the murder of a politician's bodyguard and learns that there is more at play than meets the eye, especially after discovering secrets involving the candidate's wife and campaign manager.
After being discovered in Trudy's old house, Monk is temporarily institutionalized. Once committed, he stumbles upon a four-year-old murder. Along the way, Monk is aided by various other patients at the hospital, including a man (Kevin Nealon) who mirrors those around him, a woman who gets angry easily and lashes out at people and a man who is obsessed with Santa Claus.
A billionaire computer mogul is shot dead while mugging a couple outside a movie theater, and a uniformed officer later is seen fleeing the scene. While the press hound the police about the identity of "Fraidy Cop", Monk investigates what at first appears to be a midlife crisis gone horribly wrong–until he finds out that the two cases are connected.
When a skydiver on vacation in San Macros, Mexico jumps out of an airplane, his chute malfunctions and he dies on impact in the desert. But the coroner finds water in the skydiver's lungs, saying that the boy drowned in midair. Monk is brought to Mexico, where the phrase "don't drink the water" takes on a whole new meaning.
When a circus ringmaster is shot dead by a high flying acrobat at a restaurant, Monk immediately suspects the man's vengeful ex-wife (Lolita Davidovich) of the murder. But before Monk can find out how the pretty trapeze artist committed the murder with a broken foot, he must get Sharona to overcome her fear of elephants.
Sharona's sister Gail (Amy Sedaris) lands a part in a local play that any actress would kill for. But when the actor playing her love interest literally dies on stage after Gail apparently stabs him with a real knife that was switched with a prop knife, the police are convinced she's taken her role a little too far. Sharona and her mother (Betty Buckley) urge Monk to step into the spotlight and find the real killer before the curtain falls on Gail for good.
When the publisher of the high-powered glamour Sapphire Magazine is strangled and killed on his exercise weights under mysterious circumstances, all clues lead to the infamous swinging party palace, Sapphire Mansion, and the playboy (Gary Cole) behind the magazine. But while a weekend behind the gates of the legendary estate may be every man's fantasy, it is Monk's worst nightmare, especially after his suspect threatens to release embarrassing photos from Sharona's past.
During the investigation into a carjacking over a cherry pie, Adrian is called by his estranged agoraphobic brother Ambrose (John Turturro), who is convinced that his next-door neighbor murdered his wife. Adrian must rebuild his relationship with Ambrose while investigating the neighbor at the same time.
A tow truck driver is shot dead by a roadside sniper. His truck then careens off the road and crashes into Karen Stottlemeyer's (Glenne Headly) oncoming van, leaving her in a coma. Monk, most interested by the fact that the shooter and the driver were barefoot, must find out what really happened and keep Leland from doing something that could cost him his badge.
When a death row inmate is poisoned to death 45 minutes before his scheduled execution, Monk is brought in to find out why and runs into his nemesis, Dale the Whale (Tim Curry), who will offer Monk information about Trudy if he finds who killed the inmate. The suspects, however, are endless, including the prison librarian (Kathy Baker), another inmate (Danny Trejo), and even neo-Nazis.
Monk and his friends go to New York City to discover the connection between Trudy's murder and Warrick Tennyson, whose name was given to Monk by Dale the Whale in last season's cliffhanger, "Mr. Monk Goes to Jail". As they're checking into their hotel, mayhem breaks out in the lobby and three people are killed, including the Latvian ambassador to the United Nations. Monk quickly discovers that the ambassador's coat is wet – an odd detail because minutes earlier he was standing near Monk in a dry coat. Monk provides a police sketch artist with minute details about the perpetrator's left ear – the only part of his face that wasn't covered – and Stottlemeyer pressures the New York police captain to allow them access to Tennyson in exchange for their help in the new case. However, the DA, for reasons of her own, is blocking their access to Tennyson, and only after Stottlemeyer "borrows" the keys to the captain's office and pulls out the file that he saw Captain Cage hurriedly stuff into the b...
In yet another case of murder in a room locked from the inside, a music producer is found dead with bullets in his back, head. and chest, clearly neither an accident nor a suicide. But this time there's a further twist: the dead man's pet chimpanzee, Darwin, is caught with the murder weapon in his hand. Not wanting to make a monkey of himself by falsely accusing a chimpanzee of murder, Stottlemeyer takes the chimp into the interrogation room, tempting the animal to fire what he thinks is an empty gun. Meanwhile, Disher realizes that he's inadvertently given the captain a loaded gun and panic ensues. When the gun goes off, endangering not only Stottlemeyer but Disher, Monk, and Sharona as well, Stottlemeyer is persuaded that the chimp is guilty and is ready to allow animal control to put him to sleep. Sharona, however, is convinced that Darwin is innocent. In desperation, Sharona resorts to breaking and entering to rescue Darwin, persuading the most unlikely person imaginable to take hi
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
Karen Stottlemeyer has decided to film a "cinema verite" documentary about her husband's work, but her timing couldn't be worse. The police commissioner shouts at the captain (on camera) for focusing on a routine arson fire in a wig factory and relying on Monk to solve a more newsworthy case involving a female victim whose body was cut up with a chainsaw. Monk is in even worse trouble. After presenting some useful leads involving the chainsaw victim's age and nationality, he accidentally erases several years' worth of crucial computer files, and the enraged commissioner revokes Monk's private practice license despite Stottlemeyer's protests that doing so will destroy him. With Sharona forced to return to her old job as a nurse, the devastated Monk sits in the hospital hallway all day waiting for her until, at her exasperrated insistence, he finds a job with a magazine as a fact checker. Meanwhile, having identified the victim based on Monk's information, the captain and Disher zero...
When five members of the West Coast Mafia are shot down in a barbershop, Monk is pressured by mob godfather Salvatore Lucarelli and his nephew "Fat Tony" to solve the case. But the FBI in the person of Agent Colmes is pressuring him, too. Despite Captain Stottlemeyer's insistence that Colmes is not to be trusted, Monk accepts his offer of reinstatement on the police force if he can bring down the whole gang. The only clues are a partially completed crossword puzzle and a gumball machine that was apparently used to break a back window so the killer could escape. With a Mafia bodyguard named Vince as their "babysitter", Monk and Sharona interview the sole witness, Phil Bedard, a young U.S. mint employee who tells them that he saw three men running from the scene, one of them wearing a jacket with a strange-looking number 15 on the back. Bedard also explains the heightened security at the mint: someone has stolen five double-headed pennies. Associating the numbers on the jackets with a Ch...
It's Sharona's turn to be terrified. After several frightening and mysterious encounters with a blood-soaked man that no one else can see, she begins to doubt her own sanity, and Stottlemeyer advises Monk to give her time off to restore her nerves. Monk is left with an irritating substitute nurse whose philosophy is the opposite of Sharona's: everything from Monk's requests for wipes to the obsessively systematic organization of his refrigerator has to go. Wanting Sharona back again, Monk goes to the garage where Sharona first saw the blood-soaked man and finds a clue--the silver tip from the toe of a cowboy boot. Meanwhile Sharona, who is attending a night class in creative writing, apparently forgets to turn in an assignment and seems to be misplacing objects. But when her writing instructor's husband dies of a heart attack after eating tomato soup, Sharona recognizes the plot of her missing story and realizes that she's not crazy. All she and Monk have to do now is tie together the...
When Edna Coruthers, a model employee at a giant chain store called Mega-Mart, is killed by a falling television set, Monk is called in to investigate by the store's security chief – who turns out to be his disgraced ex-partner, Joe Christie. Neither Monk nor Stottlemeyer wants to work with Christie, whom they hold responsible for some missing cocaine and the death of two police officers, and both of them disregard the evidence that Edna might have been murdered – a broken shoe heel (suggesting that the victim ran from someone or something), her dust allergy (which normally kept her from entering the loading dock where the death occurred), and the three letters (in different handwriting but with similar stamps) complaining about the victim. Twenty-seven days later, realizing that the stamps were all from the same roll and therefore from the same person, Monk reluctantly agrees to help Christie discover a suspect and a motive by working undercover as a store clerk. But he still doesn't tr...
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
After Captain Stottlemeyer is shot in the shoulder by an unknown assailant, a somewhat rattled and very angry Disher is left in charge of the investigation. Although Monk is almost as distressed as Disher, he provides very little help with the investigation, even allowing a suspect to get away. Feeling depressed and helpless, Monk decides to try a new medication that controls his OCD and eliminates his phobias but also makes him insufferably egotistical, unempathetic, and oblivious to the details that are so vivid to the "normal" Monk. Meanwhile, the suspect Disher has been pursuing is proven innocent, and the bullet taken from the captain's shoulder is traced to a gun belonging to a dead woman. Stottlemeyer impatiently checks himself out of the hospital with his arm in a sling and arranges to interview the new suspect with the help of Monk, Sharona, and Disher. Monk arrives late, dressed in a loud Hawaiian shirt and talking like a "cool cat" from the 1950s. "The Monk", as he calls him...
With Sharona in New Jersey remarried to her ex-husband, Monk has been without an assistant for three months and it's time to find a new one – if only he could find a suitable applicant. When Natalie Teeger, a thirty-something widow with an eleven-year-old daughter, arrives at his house, he thinks she's applying for the job, but she's really been sent by Captain Stottlemeyer to get Monk's help – two men have broken into her apartment in the last few days and she had to kill the second one with scissors in self-defense. Examining Natalie's apartment, Monk finds a single clue, an unused fish net caught between the sofa cushions, suggesting that the intruders were trying to steal Mr. Henry, Julie's pet fish. But why would anyone want to steal a ninety-nine-cent red herring, er, crimson marblefish? A second clue surfaces when Lieutenant Disher finds a note in the dead perp's pocket reading "2:30 Sea of Tranquility" and Natalie identifies the Sea of Tranquility as an exhibit at the science mus...
When John Ricca, author of a controversial and unfavorable biography of martial artist Sonny ("The Cobra") Chow, is found dead in his home, all the evidence points to Chow as the murderer. Unfortunately for Captain Stottlemeyer, his chief suspect has been dead for six years. While Monk and Natalie (who's more interested in being reimbursed for her business expenses than in solving the case) visit Chow's former teacher, Master Zee, who claims that Chow died in his arms, Stottlemeyer resorts to having the corpse dug up to prove that, despite rumors to the contrary, Chow is indeed dead. A dental X-ray proving that the corpse is Chow leaves Monk to figure out who tried to frame the dead man for murder. On an inadvertent tip from Disher, an avid Cobra fan, Monk and Natalie visit the Sonny Chow museum, where Monk finds two important clues – a hairbrush that has been stolen from its case and replaced with a lookalike and the stamp that the museum proprietor placed on Natalie's hand so that she...
After witnessing a Chinese gangland murder, Monk has to stay in an FBI safe house – a cabin in the woods – in the protective custody of Agent Grooms, with Stottlemeyer and Natalie as company. Awakened by a man's scream, Monk convinces Stottlemeyer and Natalie that a woman in a nearby cabin has murdered her husband. Agent Grooms, however, remains skeptical. After Grooms disconnects their telephone, Stottlemeyer locks him in the bathroom and the three "borrow" Grooms's car and set out in a rainstorm to investigate, only to get stuck in the mud on the way. Meanwhile, Disher and his new girlfriend Hayley are encountering a strange circumstance – the fortunes in their fortune cookies keep coming true. When a fortune informs Disher that an old friend is in trouble and only he can save him, Disher immediately sets out to save Monk, unaware that he's leading a pair of hitmen to the FBI cabin. After a rainy night in the car, Stottlemeyer leads Natalie and Monk through the woods toward the neighbor...
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...
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...
With her daughter's school about to be closed as a cost-cutting measure, Natalie becomes a candidate in the upcoming school board election despite Monk's fears that she'll desert him if she wins. Natalie's frustrations with a jammed photocopier and other defective equipment bought at a police auction are dwarfed by fear for her life when a sniper fires into her campaign headquarters, further damaging the equipment and killing a security guard. The only clues to the identity of the sniper are an oddly folded note demanding that "Natalie Teege" withdraw from the election and a bullet from a semiautomatic rifle made in Russia. Suspicion falls on Natalie's opponent in the election, Harold Krenshaw, whom Monk knows as a fellow patient of Dr. Kroger's. Although Monk thinks that Krenshaw is lying about his friendship with Dr. Kroger and Krenshaw admits to being an excellent shot, Monk is sure that Krenshaw is innocent because he wouldn't misspell Natalie's name. When Krenshaw passes a polygraph...
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...
While Monk is immobilized by the presence of dog poo at a crime scene, slovenly private eye Marty Eels steps in, using the dog poo (and the dog) as clues in the murder of a security guard, the robbery of a jewelry store, and the disappearance of the store owner, Harold Gumbal. With Monk tailing helplessly behind, muttering "He's cheating" and "That's impossible", Eels locates the stolen jewels, Gumbal's car, and Gumbal's body. Using Gumbal's watch as a clue, he determines the identity of one of the killers, who is then arrested and interrogated. Just as Eels is becoming a local celebrity, with Monk as "yesterday's news", Monk figures out Eels' secret and confronts him. Eels challenges him to prove it, but moments later, he runs after Monk begging for his help: the killer who's still at large wants the jewels back and is holding Eels' mother hostage. The shoe is on the other foot, and Monk must figure out where Mrs. Eels is and why she must be rescued before 8:20.
When an officer dies after drinking poisoned wine sent to Captain Stottlemeyer as a Christmas gift, the captain suspects Frank Prager, who tried to shoot him outside a bar several months earlier. Searching the crime scene for clues, Monk notes that the bullet holes seem to form a pattern, but neither he nor Stottlemeyer can figure out the message they're intended to convey. After trying unsuccessfully to talk with Prager's young daughter, Monk goes under cover as Santa Claus. This time he learns that Prager is hiding in a church with "three ladies" in front of it. But when Prager is caught and interrogated, it's clear that he had nothing to do with the poisoned wine. With the other suspects on Disher's list also eliminated, Monk and the captain are back to square one. But when Monk opens the card accompanying his gift from the Christmas party, he finds the clue that solves the case.
Monk is facing a crisis: he's down to five shirts. But Inspector No. 8, the only shirt inspector who can meet Monk's criteria for perfection, is not up to her usual standards. Sensing that something is wrong, Monk visits No. 8 on the job. The inspector, Maria Ortiz, informs him that her son, Pablo, has been imprisoned for murdering a fashion model, but she's certain that he's innnocent. Monk is chiefly concerned about his shirts, but Natalie persuades him to talk to Pablo because "it's the right thing to do." The conversation uncovers just one clue: Pablo can't read English. When Monk realizes that the killer must have been able to read an emergency exit sign, he's convinced that Pablo is innocent despite the DNA evidence used to convict him. With Stottlemeyer and Disher in tow, Monk and Natalie attempt to talk to the model's former roommate and the fashion designer she worked for, Julian Hodge. But now there's a new problem: Hodge wants thirteen-year-old Julie to model for him. Watching the rehearsal for a fashion show in which Julie will make her debut, Monk discovers a clue that points him to the real killer. When another supermodel is found dead, it's imperative that Monk find new evidence to prove his suspect guilty of both murders and set Pablo free – and for Natalie to get Julie away from the person committing the murders.
During the investigation of a murder in a junkyard, Captain Stottlemeyer punches a cop named Ryan Sharkey, who claims to be having an affair with the captain's wife, Karen. The only witness to the murder, a homeless man named Gerald or Jerry, has disappeared, but Stottlemeyer suspects businessman Michael Karpov, who is facing charges for money laundering and had a motive for killing the victim, who was scheduled to testify against him. Removed from the case and ordered to take anger management classes, Stottlemeyer asks Monk and Natalie to follow his wife, whom he suspects of lying about her whereabouts. They discover Karen having lunch with a man but are only able to photograph him from the back before being interrupted. Meanwhile, the homeless witness has been stunned and thrown from the third floor of a building but survives the fall, thanks to a corrugated refrigerator carton. Disher places Karpov in a line-up otherwise composed of police officers, including Sharkey, but Stottlemeyer, still enraged at Sharkey, disrupts the line-up before the procedure has been completed. An apple provides the clue that Monk needs to solve the murder case, and Karen reveals the identity of the mystery man she had lunch with. Unfortunately for the captain, it isn't Sharkey.
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.
When Captain Stottlemeyer suspects that a suicide is really a murder, Monk confirms his suspicions by discovering that the victim, Joanne Raphelson, was too short to have used the stool she supposedly stood on to hang herself. But the next clue, the remains of an olive, a cherry, and a cocktail onion on a stirring stick, leads Monk to suspect that the murder was committed by an astronaut, Steve Wagner. A little research reveals a motive – Joanne was about to publish a book revealing that Wagner had abused her five years earlier. Now all Monk has to do is to prove that Wagner could commit the murder when he was in outer space.
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 is called to a murder at the location where he first heard of his wife's murder, and while Monk figures out who the assassin is, he doesn't know that the one who ordered the hit is also responsible for the death of Trudy. Knowing that Monk will eventually put all the pieces together, he orders Monk's death, and when all hope seems lost, Monk discovers something which could finally end his 12-year nightmare.