Jingle me timbers! Any episode that has Monk jumping a desk and beating on someone is an incredible show! This episode first aired February 2, 2007.
Steven Weber is this episode's villain that ends up managing to kill his wife in a rather ingenious way. I am not really spoiling anything by telling you who the killer is as Monk tends to show you the murderer first thing and then the rest of the show is Monk solving the case.
Needless to say, Steven Weber's character, Max Hudson, is a Howard Stern like shock jock who meets Monk on the air after Monk is approached by the dead wife's sister, who believes that Max Hudson is responsible. The on air escapades are hysterical, as is the next 30 or so minutes
Monk takes joking insult after insult and feels like he is back in school, but he manages to approach Max Hudson and the Goon Platoon again on the air, prepared this time with a box of jokes given to him by Kevin.
But this is where the episode takes a huge turn from comedy to drama when Weber's character uses Trudy's death as a punch line. I felt Monk's anger and I was cheering when he beat the living daylights out of Max. Eventually Monk figure out that while Max had a perfect alibi, he used his neighbor's dog to commit the crime. Monk got the last word over Max Hudson at the end - "You don't look like your laughing now."
The "shock jock" combined with Monk's OCD and mannerisms did a lot for this episode, and closing it off with a such a powerful moment really made this episode great.