Having dispensed with the honorable mentions, we turn to the actual 20 best Monk episodes.
20) Mr. Monk is Someone Else (Season 8, Episode 4): This episode begins with a bang. It appears that Monk is killed in the first scene. But of course, it’s not Monk, it’s contract killer Frank DePalma, who is a dead ringer for Monk. The FBI asks Monk to go undercover, find out who DePalma’s target was, and stop the killing.
Monk goes undercover, taking on the role of a wise guy assassin. Monk discovers that the target is an elderly man with no ties for the mafia. It’s not long before everyone feels that Monk has gotten too much into character, and they attempt to pull him off the case, but Monk persists.
The mystery is one of the more solid entries of the show’s latter seasons. The highlight though is Monk finding his inner tough guy and holding his own with the mafiosos who hired him. Add in two classic confrontations with the Captain and Harold Krenshaw, and this one is definitely a keeper.
19) Mr. Monk is Up All Night (Season 6, Episode 9)
Mr. Monk is having trouble sleeping, so he heads out on a walk, and through a restaurant window, witnesses a murder. Or does he? When the Captain and Disher arrive, they find no evidence of the crime. Was it covered up or is Monk having a breakdown.
This episode, as the title implies, occurs almost entirely at night. This gives it a noirishfeeling, that makes it particularly appealing. It also has to feature perhaps the best Randy Disher scene ever when the true culprits are apprehended.
18) Mr. Monk and the Red Herring (Season 3, Episode 10)
The context of this episode does not make it an obvious fan favorite. This began the 2nd half of Monk’s 3rd Season. In the interim, Sharona had been written out of the series due to contract disagreements with Bitty Schram. This meant that the episode which introduces the “new assistant” had better be good.
The cast and crew managed to pull it off. Natalie meets Monk after killing a burglarar in self-defense. The apparent reason for the burglary is Natalie’s daughter’s fish.
The episode does a good job introducing Natalie. As a widow, she is in-tune with much of what Monk has gone through. In addition, she’s a jill of all trades which made her a valuable assistant to Monk. She had a very distinct personality and style that differed from Sharona.
The mystery is clever and quirky, making this a solid introduction for Natalie Teeger, despite the rough background that the episode aired against.
17) Mr. Monk’s 100th Case (Season 7, Episode 7): Many television shows have faced the challenge of celberating a milestone. Many just ignore it, blowing past 100 or 200 episodes like it doesn’t mean a thing. Others have had clips shows, where 4 or 5 minute new footage is package with a bunch of used footage. (This is known as the cheapest type of television episode.)
In the Golden years of television when TV programs did 39 half hour episodes a year, 100 episodes wasn’t a big deal. But given that Monk’s first season was 13 episodes and subsequent seasons were 16 episodes each, this was truly a big deal for the show’s longetivity. It was also a big deal for a reason referenced in the Season 2 episode, “Mr. Monk and the T.V. Star,” with 100 episodes, Monk would live on in syndication and create even more fans and generate millions in additional revenue.
The writer marked the event, by having a news magazine follow Monk as he solves his 100th case. The episode begins with Monk’s friends gathering around the television at the house of the magazine’s anchor to celebrate, with Monk alone at the party, and thinking something is very wrong.
The episode did a great job recreating the feel of a news magazine, and also brought back several past Monk foes back in new footage. One remarked, “Do I remember Adrian Monk? That’s like asking the Titanic if it remembers the iceberg. ”
In doing the show this way, Monk took a look back without being hokey, satisfied fans, and left plenty of room for a good mystery twist.
16) Mr. Monk Goes to Vegas (Season 3, Episode 14): Monk gets a call from an inebriated Captain Stottlemeyer stating that he knows a man murdered his wife, whose death had been assumed to be accidental. Monk and Natalie head out to investigate, but a hungover Stottlemeyer doesn’t remember what it was he’d noticed.
This episode was a lot of fun. Monk has a formidable villain in James Brolin, and Vegas setting was nicely done. Monk and Natalie also have some great scenes together. Perhaps the most notable realization what that the Captain could solve crimes as easily as Monk provided the Captain was drunk. This was reminiscent of Anthony Boucher’s character, Nick Noble.
Overall, “Mr. Monk Goes to Vegas,” offers a very even mix of comedy and mystery.
Next week: 11-15