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16 Episodes 2008 - 2009
Episode 1
Fri, Jul 18, 200844 mins
Following the death of his beloved psychiatrist, Dr. Charles Kroger, from a sudden heart attack, Monk decides to buy a house to get away from the neighbor girl, who constantly plays a Chopin prelude on the piano that reminds him too much of Dr. Kroger. The house he purchases is that of Joseph Moody, an elderly man who died recently in what the police presumed was an accident in which he fell down a flight of stairs. Needing help with a minor repair, Monk hires "Honest" Jake Phillips, a handyman who is everything but handy or honest. While learning that the house could literally be a "money pit," Monk discovers that the former owner's death was no accident, but discovers the truth too late, putting himself, and Natalie, in grave danger. Monk decides it's time to try out a new psychiatrist.

Episode 2
Fri, Jul 25, 200844 mins
Monk and Natalie are approached by Linda Kloster, wife of renowned chess grand master Patrick Kloster, who she believes is planning to murder her for the insurance money. Monk makes a promise to her that he won't let Patrick get away with the crime. Subsequently, Linda is found dead of an apparent heart attack in her bedroom, though Monk immediately suspects poisoning. In trying to find evidence to nail Patrick, Monk finds himself facing off against a foe who is much, much smarter and is able to anticipate his every move.
Episode 3
Fri, Aug 1, 200843 mins
After a late night drawing, Gold Rush Lottery hostess Marissa Kessler is killed in a random crime of passion, but Monk suspects that there's something more to her murder than is visible. But while investigating, Natalie is approached by the TV station's manager, who asks her to pick the numbers at the next lottery drawing. Strapped for cash, Natalie can't refuse, and does the job so well she is given the position full time, leaving Monk short an assistant. But Natalie eventually finds herself crawling back to Monk after she and Stottlemeyer are accused of rigging the lottery system.

Episode 4
Fri, Aug 8, 200843 mins
A boxer narrowly avoids a bomb, and Stottlemeyer believes it won't be the only attempt with a championship bout coming up. Meantime, Monk splits his time between the case and contemplating retirement when he finds he must pass a fitness exam.

Episode 5
Fri, Aug 15, 200843 mins
When Natalie is contacted by Mitch's old friend to investigate a suspicious suicide on a submarine, Natalie jumps at the opportunity and enlists Monk's help. However, things get complicated when the submarine heads off on a mission... with Natalie and Monk still on board. Monk must battle his phobias and stay focused to catch a murderer who is well within their reach.

Episode 6
Fri, Aug 22, 200841 mins
Monk is smitten with an attractive former dancer and when she's accused of murder, he agrees to help her, even though all the evidence points to her, and continues searching--even after she confesses to the crime.
Episode 7
Fri, Sep 5, 200842 mins
As Monk is working on his 100th case, wherein he is looking for a serial killer, a TV news crew records him and interview the people whom Monk caught and those who know him. The anchorman who is married is making a pass at Natalie. As the investigation goes on, Monk thinks that one of the victims might not have been killed by the one they're pursuing but the M.O. (modus operandi) resembles the killer's. So someone somehow found out about it and made it appear that he killed the person. But the thing is only someone working the case could have known about it.

Episode 8
Fri, Sep 12, 200841 mins
Monk runs into Harold Krenshaw who tells Monk he went to a hypnotherapist who cured him. Monk goes to see the same hypnotherapist who hypnotizes him as well. After the treatment, Monk begins to behave like a juvenile because reversion therapy has taken him back to his happier childhood days. Now Monk has taken on the mannerisms of a child while investigating the disappearance of a woman who returns shortly after her husband has been killed.

Episode 9
Fri, Nov 28, 200844 mins
Monk's Christmas spirit, or lack thereof, is challenged when he takes a case from three homeless men who believe their friend was murdered, and Leland's epiphany sends him on a mission.

Episode 10
Fri, Jan 9, 200944 mins
Steve Zahn is Adrian's newly found half-brother who escaped prison and is accused of killing a woman while on the run. He turns up at Adrian's house seeking his aid. Zahn is very funny and the situations between him and Monk are wonderfully comic as Adrian tries to deal with Zahn and his outrageous shenanigans.

Episode 11
Fri, Jan 16, 200941 mins
When Natalie inadvertently helps someone who is stealing a bike, she promises the owner she will find it. So, she makes Monk help her. While tracking down the thief, Monk is shot in the leg. He then has to go around in a wheelchair and he makes Natalie push him around which drives her to the breaking point. Later the man who stole the bike is found dead.

Episode 12
Fri, Jan 23, 200944 mins
Monk's recent, transforming friendship with neighbor Marge Johnson begins to seem suspicious after he's brought in to consult on two murders.

Episode 13
Fri, Jan 30, 200943 mins
Monk dips his toe into male bonding when he attends the playoffs with Leland, but a murder distracts them from the game and its solution may be the only way to ensure the championship.

Episode 14
Fri, Feb 6, 200943 mins
Monk gets a call from a man who bullied him when he was a kid. He's still affected by it. He's uneasy when he goes to see him. The man wants to hire Monk to follow his wife who he suspects is hiding something from him. Monk accepts to rub his nose in it. And when he follows her he discovers she's hiding something but Monk thinks there's more going on.

Episode 15
Fri, Feb 13, 200944 mins
Monk's neighbor Kevin Dorfman has been doing the books at a magic club. He questions one the magicians, Torini, about how the load he came back with from a recent tour in Asia was heavier as opposed to it when he left. Torini tries to sidestep the issue by telling Kevin, who's been training to be a magician, that he has to go out of town and that he wants him to fill in for him. Kevin invites Monk and on the night he's supposed to go on, Kevin is killed. Monk, who found Kevin's body, suspects Torini because he saw someone walk out of Kevin's dressing room before he went in and while he didn't see his face, one of his gestures is like Torini's. But Torini was not only out of town, he called the club and spoke to everyone on the speaker, so how could he have been the one Monk saw?

Episode 16
Fri, Feb 20, 200943 mins
Monk is desperate to keep the parking garage where Trudy was murdered so many years ago from being demolished for a playground which has huge citywide support. He thinks he has a councilwoman behind his efforts but when she suddenly vanishes, he must deal with a ditsy assistant to the councilwoman. When a vacationing couple turns up dead, Monk begins to think their murders have to do with the missing councilwoman. But do they? And is Trudy's place of murder a rightful reason to stop a good community development project for neighborhood children?