Restless over the unending nature of his work, Monk takes Dr. Kroger's advice and takes up a hobby, art. While most people mock his unconventional efforts, a rich man named Lovak begins buying up every painting. Could this be related to the murder of the owner of the junkyard where Monk got his materials?
This episode includes examples of the following tropes:
- Alone with the Psycho: Monk remembers that one painting in Lovak's van had been in the junkyard where he got his canvases. This makes him realize Lovak had an ulterior motive, and then Stottlemeyer and Disher arrive with the news that Lovak is a mobster. Immediately thereafter, they realize that Natalie has the only Monk painting that Lovak hasn't bought. Cut to Lovak trying to buy it and then pulling a knife on Natalie when she refuses.
- Artistic License – Law: Deadly booby traps are extremely illegal, and a police captain with as much experience as Stottlemeyer would know that. In reality the junk yard owner would have been arrested after the first killing.
- Artsy Beret: Monk dons a beret once he becomes convinced he's an artistic genius. He refuses to wear it tilted, however.
- Blown Across the Room: The shotgun booby trap that Lovak's goon sets off knocks the guy back a good couple of feet.
- Booby Trap: Bennie Wentworth, the owner of the junkyard the canvases created to make counterfeit cash wind up at is fond of these. One of them, a shotgun on a tripwire, kills a henchman of Lovak's as he tries to break in to take it. This forces Lovak to get his hands dirty and kill Wentworth himself, although the canvases are gone by then.
- Counterfeit Cash: Lovak wanted the paintings because they were painted on the same kind of paper the US Treasury uses, and the paper would thus be valuable for counterfeiting money. This may not be as Artistic License as it may sound, as US Federal Reserve Notes are not printed on paper, but a blend of cotton and linen... like canvases are.
- Freeze-Frame Bonus: At the end of the episode, if you pause it at the right time you can actually see the Natalie Painting.
- I Kiss Your Hand: Lovak regularly kisses Natalie's hand when saying hello or goodbye.
- Irony: In a sense, Lovak's advice to "look at your art with new eyes" is what finally gets Monk to open his eyes that he's not an artistic genius, and that Lovak had an ulterior motive for buying his paintings.
- Jerkass: Bennie Wentworth is kind of an asshole. He sets up deadly booby traps all around the junkyard and tells his Hispanic employee to speak English in a somewhat racist sounding fashion.
- Kill It with Fire: In the epilogue, Natalie tries to burn the portrait Monk made of her so it will never see the light of day.
- Language Barrier: Bennie's assistant Hector is a witness but doesn't speak English, and no one on the team speaks Spanish. Randy thinks he does, but he really doesn't.
- Make It Look Like an Accident: When Lovak kills Bennie Wentworth, he tries to make it look like Bennie walked into one of his own booby traps while drunk. Monk isn't fooled because the knife wound on Bennie's chest is a good six inches higher than the knife on the booby trap.
- My Hover Craft Is Full Of Eels: Randy offers to translate for Bennie's employee, Hector Morales. He doesn't do a very good job of it. Luckily, Hector speaks English well enough that Stottlemeyer can communicate with him.
- Skewed Priorities: Natalie attempts to burn Monk's unflattering portrait of her, even after Randy reminds her that the portrait is the only one of Monk's paintings remaining and will serve as important evidence in the trial.
- Terrible Artist: Monk is treated as this, though for a while he's too blinded by Lovak's flattery to see it. In reality, Monk's artwork is criticized heavily by other characters, but his use of straight lines, simple geometric shapes, and contrasting colors are actually decent examples of Minimalism, a form of post-modern art; he can't really be blamed for his teacher's apparent fondness for Expressionism.
- The Unreveal: We never get a good look at how bad Monk's portrait of Natalie is, just comments that it looks like Stottlemeyer or Miss Piggy.
- The Voiceless: Arkeny Stasya, the henchman Petya sets to retrieve the canvases, doesn't talk... unless you count the grunt he makes after taking a double barreled shotgun blast to the chest.
