Monk had many great episodes across its eight seasons. The series followed the titular character, a former police officer played by Tony Shalhoub, who suffers from multiple mental afflictions stemming from an anxiety disorder. Despite other people judging him for his phobias, Monk is the most observant and logical person in any room, able to solve even the most impossible cases as a consultant for the police department.
The innovative comedy drama produced a total of 125 episodes between 2002 and 2009. Many of these were met with critical acclaim and cemented Adrian Monk as a cultural icon, to the point the character returned more than a decade after the end of the show for a feature-length special called Mr. Monk's Last Case. The best episodes of the original show have fascinating mysteries, stellar performances, and engaging scenes.
20 “Mr. Monk And The Girl Who Cried Wolf”
Season 3, Episode 6
For Monk fans who want to see a scary episode, possibly the scariest of its entire run arrived in the third season with "Mr. Monk and the Girl Who Cried Wolf." The scary moments here concern Sharona, who believes she is losing her mind when she thinks that a dead man is following her around. Unlike many episodes of the fun detective series, this one has some jump scares and goes a little far when it comes to showing the dead man with the screwdriver in his neck.

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However, the entire dead body is a plot by Sharona's creative writing teacher, who is gaslighting her. The teacher plans to kill her husband using a story that Sharona wrote, but she knows she needs to discredit Sharona so the police won't listen to her if she comes to them about it. The entire episode is heartbreaking as well, with Monk having no idea how to help his friend until he finally figures the plot out. The episode also has some very funny moments, showing how good the show is at balancing its focus.
19 “Mr. Monk Goes Home Again”
Season 4, Episode 2
"Mr. Monk Goes Home Again" is a Monk Halloween episode, and it really plays off the relationship between Ambrose and Adrian in the series. Ambrose (John Turturro) deals with OCD just like his brother, which makes him just as observant and brilliant. However, he also has a severe form of agoraphobia and won't leave his home while keeping all his father's mail and other items, believing he will one day return. This episode sees Ambrose telling Adrian that their dad called and wants to see them.
Ambrose is also in danger here, making this a much more personal episode for Adrian Monk, which always makes for the best of the show's installments.
This episode has some very funny moments, such as Adrian refusing to let it go when people refer to Frankenstein's Monster as simply Frankenstein. Ambrose is also in danger here, making this a much more personal episode for Adrian Monk, which always makes for the best of the show's installments. Also, since Ambrose is not a series regular, there was always a fear he could die since the show isn't always protective of guest stars. However, the episode's ending, with Ambrose finding a letter from his dad, was extremely emotional.
18 “Mr. Monk And The Red-Headed Stranger”
Season 1, Episode 12
What most people about "Mr. Monk and the Red-Headed Stranger" is that Willie Nelson appears in a guest role. In a first-season episode, the show bringing in Nelson showed how big the guest stars would be over the years, and this one set the bar high. What was even more important is that Willie played himself, and he was accused of murdering his tour manager, Sonny (David Anderson), who he caught stealing money. Even better, he wasn't playing a character but a fictional version of himself.
Monk is called in to help clear Willie's name, and he does so when he proves that the blind witness who said she heard Willie's voice was not blind at all. However, what makes the episode great isn't just Willie's appearance or the mystery of the blind woman but how all this ties into a much bigger puzzle that Monk has to solve to learn the true identity of the murderer. Not only was this one of the rare episodes where the murderer might be justified in a morally ambiguous ending.
17 “Mr. Monk And The Astronaut”
Season 4, Episode 14
The Monk episode, "Mr. Monk and the Astronaut" brings in an actor who will become a very familiar face in the next few years. Jeffrey Donovan (Burn Notice, Law & Order) stars as Steve Wagner, an astronaut who becomes a nemesis to Adrian Monk. This is one of the episodes where Monk plays with the format of the classic detective series Columbo. For those who never watched that classic mystery series, Columbo showed who the murderer was at the beginning of the episode.
However, like Columbo, Adrian Monk has to figure out how the killer did it to clear the way for police to arrest him and have a good enough case to convict. Donovan is great as the villain, and his bullying and antagonism of Monk made him one of the most hated antagonists to ever appear in the series. He even gets the kids in Julie's class to start bullying the detective. This makes the moment when Monk proves Wagner is guilty and stops him one of the most triumphant moments in Monk's history.
16 “Mr. Monk And The TV Star”
Season 2, Episode 12
When it comes to Monk episodes that pull together everything that the show does well, this is right up there. Billy Burke (Twilight) stars as an actor named Brad Terry. Terry plays a character in a fictional police procedural called Crime Lab S.F. This episode offers a lot of fun humor, and Monk pokes fun at other police procedurals. Since it plays as one itself, it really makes all the jokes feel all the more familiar. The mystery comes when Brad's wife is murdered while he is outside talking to the paparazzi.
However, Monk believes that Brad killed her despite being outside when she appeared to have died. Not only was Billy Burke a special guest in this episode, but it also features a ing role by Sarah Silverman, who appears as Marci Maven, an obsessive fan of Terry's. Between the inside jokes about cop shows and Monk's very difficult mystery to solve, this ends up as one of the best episodes that fans can revisit and often find something new to laugh about.
15 "Mr. Monk Meets Dale The Whale"
Season 1, Episode 3
Monk season 1, episode 3 "Mr. Monk Meets Dale the Whale" was one of the first episodes to delve further into the murder of Adrian Monk's wife, Trudy. While the series features mysteries of the week for Monk to solve, the overarching mystery of the show is the very event that triggered Monk's anxieties. Monk spends his spare time trying to find out everything he can about Trudy's unsolved death, and while it starts here, it takes almost the entire show to solve that mystery.
The episode introduced Monk's primary criminal nemesis, Dale "the Whale" Beiderbeck, played perfectly by Adam Arkin. The central mystery is not one of Monk's best, but "Mr. Monk meets Dale the Whale" neatly expanded the show's lore, while offering a truly great villain that would return to the series twice more.
14 "Mr. Monk And The Marathon Man"
Season 1, Episode 8
Monk season 1, episode 8 "Mr. Monk and the Marathon Man" demonstrated early in Monk's first season the potential for comedy inherent in the show. It is the first example of Monk stepping outside of his typically insular characterization by introducing him to one of his heroes - played by Zakes Mokae.
Monk's practical nurse Sharona spends a lot of the early episodes reassuring everyone around them that Monk is working on understanding and moving beyond his fears.
Monk's attempt to recreate the episode's murder is a particular highlight, deriving much comedy from the frustrations of Sharona (Bitty Schram) - a common theme in the first season. Monk's practical nurse Sharona spends a lot of the early episodes reassuring everyone around them that Monk is working on understanding and moving beyond his fears. Some of them, she even reassures people, that, "he's almost there, we're making good progress on that one," but this episode shows that he has a long way to go, and Sharona knows it.
13 "Mr. Monk Takes A Vacation"
Season 1, Episode 9
Monk season 1, episode 9 "Mr. Monk Takes a Vacation" is an homage to Alfred Hitchcock's Rear Window. A murder spied through a telescope, with a crime scene that even someone who is germophobic like Monk considers clean, provides a highly memorable primary narrative and an equally satisfying solution. Polly Draper's performance as the hotel security officer is especially enjoyable, particularly the way she and Monk soon influence each other's behavior.

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The episode is also notable for centering Sharona's son, Benji (Max Morrow) throughout. It's made clear as early as episode two that Monk has something of a friendship with Sharona's son. He even calls him in one episode to have Benji walk him through Sharona's chicken pot pie recipe. Because of that, it's nice to see his character expand beyond just knowing that Monk is his mom's patient.
12 "Mr. Monk Gets Cabin Fever"
Season 3, Episode 12
When Monk is placed into a witness protection program for his own good, he, Natalie (Traylor Howard), and Detective Stottlemeyer (Ted Levine) are sequestered in a remote cabin in the woods in Monk season 3, episode 12 "Mr. Monk Gets Cabin Fever." The episode's principal murder is slightly absurd, but certainly not Monk's most ridiculous crime during its run.
Nevertheless, the final wrap-up is rather satisfying and features possibly the most dramatic final scene in any Monk episode - depicting an action-packed shootout fairly atypical for Monk. The episode allowed the viewers to have a change of scenery, a change of pace, and a big action sequence, breathing some fresh air into the show three seasons into the run. Monk was able to successfully make deviations from its format where other more typical crime procedurals cannot.
11 "Mr. Monk And The Employee Of The Month"
Season 3, Episode 7
Enrico Colantoni makes a very memorable guest appearance as store detective Joe Christie in Monk season 3, episode 7 "Mr. Monk and the Employee of the Month." Colantoni is no stranger to crime shows now with roles in Veronica Mars and Flashpoint, but his role here is a little different. The interplay between him and Monk is exceptionally noteworthy, proffering an opportunity to develop Monk emotionally and expand his backstory.
A lot of humor is derived from putting Monk outside his comfort zone, which at this point in the series had not yet become tiresome. Every episode strived to make Monk just uncomfortable enough to help him progress in dealing with his anxiety and keep the audience entertained. The final resolution is not one of Monk's strongest, but the process is an enjoyable emotional journey, with a slew of entertaining ancillary characters.