Bart gets a hold of Denis Leary's cellphone while working at a country club to buy his own, but when Leary himself confronts Marge about Bart tricking him into playing in crappy roles, Marge becomes a more controlling mother and Bart runs off to the ancient South American city of Machu Picchu.
Tropes:
- Aesop Amnesia: Marge learns yet again not to be so smothering and overprotective towards her children.
- Anti-Smother Love Talk: Marge has a Maybe Magic, Maybe Mundane dream in which she gets one from a South American ghost.
- Both Sides Have a Point: Marge isn't wrong in monitoring Bart since he regularly played pranks and put either himself or others in peril for his own amusement, hell, he even got the phone by stealing it in the first place (albeit because it was thrown at him and he didn't give it back rather than outright stealing it on his own accord). However, Marge still invaded his privacy, violated his rights and restricted his personal life because she was being overcautious and overprotective of him.
- Chekhov's Gun: Lisa's dream of going to Machu Picchu provides the whole engine for the second half.
- Continuity Nod: After not having made a prank call since Season 13's "Homer the Moe" note , Bart relapses big-time, getting a bar directory and using his new cell phone to harass bartenders all over the world.
- Easy Come, Easy Go: Bart tries to earn enough money for a cellphone by finding lost golf balls at the golf course, only for Willie to confiscate his haul, stating that it's his territory.
- Format-Specific Joke: Bart says of his new phone, "You can even watch commercials on it!" and holds the phone up to demonstrate, with a zoom into the screen cuing the first ad break. This is lost on DVD and Disney+.
- Idiot Ball: Marge, she mistook a bird wearing Bart's tracking chip as him. All well and good but the bird was able to reach the Shelbyville Bird Sanctuary in mere minutes and was able to reach another country entirely. If she had been monitoring Bart for a week then she'd know this is an impossible feat and out-of Bart's character.
- Irony: After spending most of the episode playing pranks and being under Marge's watchful eye, Bart ends up home alone while the rest of the family are on a wild goose chase, and since he's all alone, he thinks he can do whatever he wants. Of all things, he chooses to take a bath, then go to bed early without TV, which would be like if Homer was locked in a candy store overnight and only ate the sugar-free candy.
- Jerkass Ball:
- Bart starts using Denis Leary's phone to cause a ruckus while pretending to be Dennis Leary, drives a forklift with Milhouse on it, tricks Leary into playing bad roles, and finally leads his family on a search for him and enjoys his time alone at home without being concerned over how worried his family are over him.
- Marge activates the GPS in Bart's phone and uses it to spy on him around the clock and feels absolutely no shame for violating her son's privacy whatsoever.
- Lisa learns her family was chasing a bird called a Scarlet Tanager and its migration pattern leads to Machu Picchu, which Lisa had expressed interest in visiting earlier in the episode. She "conveniently" neglects to tell her family this so she can go on the trip she wants.
- Although it's a quick gag before the end and Negative Continuity (or them racing back) will fix it, the Simpsons still left Maggie (a baby) in Peru, and don't really start to catch up on that until they are back in the United States.
- Jerkass Has a Point: Marge violating her son's privacy is treated bad, but that first thing she spotted was Bart driving a forklift with Milhouse on it- he really needed supervision. It's not even Bart's phone; he essentially stole it from Denis Leary and profited from it to give the actor grievance.
- Karma Houdini: Nobody ever finds out that Lisa discovered Bart's ploy early on and deliberately withheld the truth to force her family to follow the bird's migration route to Machu Picchu, a dream destination of hers.
- Leaning on the Fourth Wall: Bart cues the first ad break with the discovery that he can watch commercials on his new phone.
- Mood Whiplash: Bart is left alone at home while the rest of the family is in Machu Picchu. "Night is scary. DAY IS AWESOME!" three times in a row.
- My Beloved Smother: The B-plot has Marge learn not to be so smothering toward Bart.
- Mythology Gag: It's not the first time Australia hears it from Bart.
- Nice Day, Deadly Night: Parodied; Bart is left home alone and becomes afraid of nature at night, resulting in an Overly Long Gag of Bart afraid in the dark and happy in the day ("Night is scary." "Day is awesome!")
- The Punishment Is the Crime: Not content to remove the tracking device from his phone, Bart attaches it to a bird, sending his worried family on a wild tanager chase while he enjoys having the house to himself. What he doesn't realize is that the bird is migrating, resulting in his being left alone for two whole weeks as they fruitlessly search for him in South America. Marge doesn't even bring it up with him when they get home as it's clear he's been punished enough.Bart: Never leave again.
- Serial Escalation: After Lisa finds out Marge and Homer are spying and keeping track of Bart through his phone, Marge comments it's not wrong to keep track of your loved ones. Cut to a camera hidden in the darkness of the basement showing Moe spying on Marge's movements, happy to know he agrees with her. Cue to Moe being monitored by the police adding an extra year to every perverted sentence he says.
- "Shaggy Dog" Story: Bart finally gets enough golf balls and is ready to turn them in for money, but they are confiscated by Groundskeeper Willie (or Greenskeeper Willie, working at the golf course outside of school hours).
- Shout-Out:
- The Swedish bar that Bart prank calls is a reference to Swedish film-maker Ingmar Bergman. When the bartender calmly threatens Bart over the phone, the camera angle of him with a bar patron in the background looking straight into the camera references Bergman's 1966 film Persona.
- In addition, the Australian bar is a shout-out to "Crocodile" Dundee, complete with a bartender who resembles the title character.
- Something We Forgot: The family goes to and from Machu Picchu looking for Bart, and once they are back on Springfield Lisa asks where Maggie is, with Homer being unable to answer. Gilligan Cut to Maggie, who was left behind in Machu Picchu, being worshipped by an indigenous cult.
- Trauma Swing: Played for Laughs; after Homer and Marge have tracked Bart's movements and blocked his fun at every turn the entire week, Homer watches Bart's icon on the screen and tries to figure out why Bart has been spinning in place for some minutes, asking "What's his angle?" The camera pans to the basement window to show Bart spinning miserably in a tire swing in the backyard.
- Unexplained Recovery: The first episode to have an appearance from Dr. Nick after he was supposedly killed off in The Simpsons Movie.
