Homer gets into the Internet by becoming an online gossip columnist-cum-conspiracy theorist, whose stories land him on a bizarre island for people who know too much (and is modeled after the one from the TV show The Prisoner).
- Accent Adaptation: In the German dub, the Homer doppelgänger instead speaks with an Italian accent, calling Marge "schatz-signorina" instead of "honey-fräulein", offering to take Marge out to a "ristorante" and instead of "efficient German sex" they will have "Sex auf Italo".
- Awesome, but Impractical: "The Island", as expected of a full-blown homage to The Prisoner, has Rover. Unlike its appearance in "The Joy of Sect" where its menace had been played straight (although accidentally capturing poor Hans Moleman instead of Marge), in this episode Homer is able to destroy it by popping it with a plastic fork and the overseers of "The Island" actually question themselves what the hell were they thinking when they made it.
- The Bad Guy Wins: All of the Simpsons are trapped on The Island, not that they mind, apart from the drugging.
- Black Comedy: Ned, reading Homer's website, is happy to hear he was right about flu shots being mind-control serums. He then asks a bedridden, sickly Rod and Todd if they're happy he didn't get them vaccinated. The two shiver and agree, and then Todd says, "Mommy?" On the commentary, the writers wondered if they went too far with that gag.
- Cassandra Truth: Homer's flu vaccination "rumor"note , which he made up, turns out to be true.
- Call-Back: Homer somehow drove a boat up to his driveway◊, just like what Ned Flanders did◊ back in "Alone Again, Natura-Diddly".
- Complexity Addiction: When Number 2 explains his organization's version of the flu vaccination conspiracy (with details like mind-controlling people into going in a shopping frenzy at Christmas, hence why they do shots at that time, and it's implied that it's just one step of whatever is the full plan), Homer points out that it's a needlessly complicated scheme.
- Did Not Think This Through: Homer's reporting as Mr. X ends up winning an award, but because Mr. X is anonymous the money will be given to charity. Homer exposes himself as Mr. X the moment Mayor Quimby mentions this, and thus is unable to get any more real news afterwards because people are wary to talk to him. He thus decides to make fake news... and one of the false facts he writes gets him kidnapped by a Nebulous Evil Organization.
- Dumbass Has a Point: Number 2 explains that they use flu vaccinations right before Christmas to mind control people into a frenzy of shopping. Homer calls this needlessly complicated.
- Epic Fail: Rover is about to get Homer, but he pops it with a fork.
- Failed a Spot Check: The "Mr. X" webpage actually shows Homer's face for a second before the bag that keeps him "anonymous" pops over his head. People still label him a mystery up until Homer exposes himself as Mr. X to get an award's money prize.
- Fake Crossover: Patrick McGoohan guest stars, reprising his role as Number 6. Apparently the reason why he was imprisoned was due to inventing a bottomless peanut bag.
- Gainax Ending: The whole Simpsons family end up on The Island.
- Gilded Cage: "The Island" is a pretty comfortable place to live (or at least only the Simpsons believe that) as long as you don't mind the constant random druggings. Or other psychedelia. Or being hunted down by the conspiracy if you manage to escape.
- Gosh Darn It to Heck!: Homer calls his fake news "bullplop" when he meets Number Two.
- Groin Attack: Homer defeats his doppelganger with one of these.Homer: If I know me, he won't like being kicked in the crotch! [Homer does just that]
- Halfway Plot Switch: From Homer becoming an undercover reporter (and later creating fake news to try to keep his fifteen minutes of fame, which is instantly showcased to have pretty harmful consequences) to a homage to The Prisoner that, while still being a consequence of the aforementioned fake news, comes completely out of left field.
- Holding Back the Phlebotinum: It is this or because they knew too much about the conspiracy that is the reason the numbered people were taken to The Island. Number 6 is there because he invented a bottomless peanut bag and one other number is there because she invented a method to create better fuels out of water.
- Honest John's Dealership: Homer buys a computer from a place called "Honest John's Computers". The computer itself is free, as long as the client signs up for an internet plan that costs several thousand dollars.
- It's All About Me/Kick the Dog: When Marge brings up her concern on how Homer chose to take the prize that could've been used to help starving children, Homer proudly states that they're with God. This sadly implies Homer would sacrifice the lives of millions of children for his own selfish desires.
- MacGyvering: Number 6 managed to create a sea-worthy escape raft by stealing lots of plastic cutlery and sewing together body hair. Homer is able to destroy Rover by using one of the forks the raft is made of.
- Morton's Fork: When Homer goes to the Springfield Police Department's homepage, it has Chief Wiggum asking him to tell them whether or not he's committed a crime and wants to turn himself in. Picking "no" leads to the site assuming he committed a crime but doesn't want to confess that he did and telling him that a paddy wagon is speeding toward his home, before asking him if he wants to buy some merch during the wait.Digital Wiggum: You have the right to remain fabulous!
- Mythology Gag: Number 6 said he's been working on his secret raft for 33 years. This episode aired in 2000; 33 years prior to that was 1967, the year The Prisoner was first broadcasted.
- Nebulous Evil Organization: The conspiracy that mans "The Island". It has the aforementioned super-secret facility, enough connections within the medicine industry and the government to influence when vaccines are supposed to be provided to the people (which is explicitly mentioned is one step of an already absurdly complicated plan to Take Over the World) and technology including the Rover and robot animals that they use to gas and dart anybody they want to kidnap and perfect replicas of buildings that they use to trap people for the same reason.
- Noodle Incident: Bart once got suspended from school because he had a knife in his locker.
Number 6: That's the third time that's happened!
- There's also Number 6's reaction to Homer stealing his escape raft.
- Shout-Out: Homer tries to talk to his computer by using his mouse as a microphone, just like Scotty in Star Trek IV: The Voyage Home.
- Skewed Priorities: Homer believed stale bagels to be more important than Krusty's involuntary manslaughter cases.
- Spit Take: Parodied. Upon seeing how much Homer's new computer costs, he drinks some coffee and spits it.
- Strange-Syntax Speaker: Homer's German doppelgänger starts talking like Yoda for some reason.Bart: There's something really different about you, Dad.
Doppelgänger: I am a new tie wearing.
Bart: ...Oh, yeah.
Homer: No one can silence me but me.
Doppelgänger: That arranged can be!
- Took a Level in Dumbass: This episode really exemplifies how Homer as gone through this in the modern era. Homer is really Too Dumb to Live in this episode. While he was never that intelligent, in this episode hes driving a computer behind his car and then decides that just making up news for the sake of maintaining his fifteen minutes of fame (which are then demonstrated to be endangering other people's lives without taking into account the abrupt turn into full-blown insanity that is the homage to The Prisoner) is a good idea.
- Ungrateful Bastard: Number Six is the one man that Homer talks to on the Island that isn't a psychotic conspiracy member, and he shows his escape raft to Homer with full intent for them to team up and escape. Homer steals the raft while Number Six isn't looking, halfway through that particular part of the speech.
- Unusually Uninteresting Sight: As Homer exclaims how excited he is to make his webpage while ignoring the copyright issues he may run into, a saddened Bart narrates about his day at school and how he took a swing at a cop for feeling angry. Homer and Lisa both ignore him.
- You Are Number 6: Homer starts repeating the "I am not a number!" catchphrase before he notices his Number 5 badge, which he rubs in Number 6's face.