Monk meets one of his heroes: Willie Nelson, Trudy's favorite singer... and has to clear his name in a murder investigation when his crooked manager turns up dead in an alley and a blind witness accuses him of involvement.
This episode includes examples if the following tropes:
- Actor Allusion:
- Monk asks if Willie smells anything in the tour bus, to which Nelson replies "no, and neither do you." This is a reference to Willie Nelson's famous affinity for marijuana.
- In describing Mrs. Mass's screaming, Willie compliments her "pipes." She's portrayed by Jackie Richardson, a gospel and blues singer.
- And This Is for...: Mrs. Mass tells Sonny that her first bullet is for her family, who he killed.
- As Himself: Willie Nelson and more than one of his bandmates appear as themselves.
- Asshole Victim: Sonny Cross gets killed because he got away with a slap on the wrist after killing the murderer's family in a car accident and leaving her blind.
- Awesome Music: Monk and Willie Nelson serenade Trudy at the end of the episode.
- Chekhov's Gun: The checkout clerk mentions Mrs. Mass concussing herself in the store a short while ago. It turns out that the same accident somehow fixed her sight in one eye.
- Chekhov's Gunman: The streaker. Initially, he's just an annoyance to Stottlemeyer and the police force, but then Monk uses his penchant for naked running in a ploy to show Mrs. Mass can actually see. To Sharona's embarrassment, he also turns out to be the guy she's been dating all episode.
- Continuity Snarl: Monk hires a streaker to solve the case, which seems inconsistent with the Season 3 episode "Mr. Monk and the Naked Man," which revolves around Monk's pathological hatred of nudists.
- Due to the Dead: As thanks for clearing his name, Willie Nelson and Monk play music at Trudy's grave.
- Everybody Has Standards: Mrs. Mass may despise her victim, but even she thought it was wrong for Willie Nelson to be framed for her murder, to the point she felt guilty for it and was relieved when Monk solved the case.
- Graceful Loser: Mrs. Mass is the only killer on the show who thanked Mr. Monk for solving the case. She said that she was feeling guilty about framing Willie Nelson, who was innocent. When everyone offers her a consolation for turning herself in peacefully, Mrs. Mass's only has one humble request: that her jail cell will have a window, so she can always appreciate her newly-restored sight.
- I Am Spartacus: Everyone in Willie Nelson's band claims to be him when the police come to arrest him. The police don't buy it and arrest the real Willie Nelson.
- Obfuscating Disability: Monk realises Mrs. Mass isn't blind because she was able to offer the correct hand to shake the Captain's uninjured hand on instinct. It turns out she regained part of her vision and kept it secret so she could kill Sonny Cross for the drunk driving incident and escape punishment.
- Take a Third Option: Monk tries to invoke this due to the first option being seemingly impossible and the second being personally unpalatable to him, but fails (albeit it eventually turns out that they were mistaken about the first option):Stottlemeyer: It's either (a) the blind woman who has zero motive or it's (b) your friend the red-headed stranger.
Randy: Who had motive, means, and opportunity, and was identified by the only witness at the scene.
Stottlemeyer: A or B, Monk.
Monk: I think it's C.
Stottlemeyer: What the hell is C?
Monk: I don't know yet.
- You Just Told Me: Monk is able to prove Mrs. Mass isn't blind by having the streaker run past and showing Captain Stottlemeyer that she reacts, just as one would expect for a sighted person.
- You Killed My Father: Mrs. Mass's last words to her victim is to let him know he killed her family.