Karen Stottlemeyer comes to her husband with a request — check into the death of Miles Holling, the oldest man in the world. An investigation reveals that he was murdered. Stottlemeyer and Monk dig deeper into the case, while Stottlemeyer grapples with his problems about an old case and his marital difficulties with Karen.
This episode includes examples of the following tropes:
- Adopted to the House: Monk lets Stottlemeyer stay at his house after Karen throws him out because he helped him after Trudy died. Unfortunately, they quickly drive each other crazy.
- Broken Pedestal: The Mayor has this for Dennis Gammill when he learns that, aside from killing George Rowe and the world's oldest man, he ran over a boy while drinking under influence. When Dennis desperately implores that the Mayor has known him throughout his career, the latter coldly replies "I don't even know you..."
- Deceased Parents Are the Best: The victim's octogenarian son may not be a "baby boy" anymore, but the way he speaks highly of the victim, one can feel they shared a special bond as father and son, a bond that's had 80 years to mature with age.
- Fright Deathtrap: The Scared Stiff variant was attempted on the oldest man in the world. It didn't work, so the intended victim got smothered with a pillow instead.
- Heroic BSoD: Leland has a cold case about a valedictorian student being killed by a drunk driver, and this combined with Monk's greater skill as a detective, left him frequently depressed. The fact that he was having marital problems stemming from not watching one of his wife's terrible documentaries (which turned out to be a Chekhov's Gun to finding out the murderer for both their current case and his cold case) that forced him to stay with Monk didn't help matters much.
- Lap Pillow: Stottlemeyer questions why Monk insists on leaving the coffee table crooked when everything else in the house is perfectly neat and organized. The end of the episode reveals that Trudy would sometimes pull one end of the table toward the couch and put her feet up on it so Monk could rest his head on her lap.
- Mugged for Disguise: A "murdered for disguise" variant. Deputy mayor Dennis Gammill poses as a guard to kill the oldest man in the world without being noticed. Of course, to gain access to the man, he had to kill one of the nursing center's real guards and steal his security pass, and also his uniform.
- No Warrant? No Problem!: Monk and Stottlemeyer show up at the house of George Rowe, following a lead in the death of Miles Holling. Stottlemeyer sees a messy room through the window, suggesting a fight. Monk briefly challenges Stottlemeyer on if they have enough probable cause to enter without a warrant, then they enter.
- Soundtrack Dissonance: The episode has the world's oldest man being suffocated with a pillow....while the room's gramophone plays a very inappropriate upbeat piano piece in the background.
- Stealth Insult: When Stottlemeyer finally snaps from the pressure of living under his roof, he gives an outraged series of these to Monk. He claims that Trudy deserves to be nominated by the Vatican for "Sainthood" because Monk is "impossible [to live with]". Then, he calls him "the world's best marriage counselor", saying all people have to do is live with Monk and they'll never complain about their spouses again.