The episode is both a parody of, and an homage to, the 1960s TV series The Prisoner. Patrick McGoohan voices Number 6 in the episode, reprising his character from The Prisoner (In the episode, "The Village" has been replaced by "The Island").
When Homer is sailing away, the boss of the clan is watching him from a big building with a round window, and is trying to stop him using different things. This is a reference to the 1997 movie The Truman Show, when Truman Burbank is trying to escape from the fake town.
Number 6's boat took 33 years to built according to him. This is a reference to the year that The Prisoner first aired on TV (1967).
When the boat is later stolen by Homer, Number 6 proclaims that it's the third time the boat has been stolen from him. In The Prisoner, Number 6 managed to escape from The Island twice with a boat in different episodes.
The computer salesman says one of his computers is the kind astronauts use to do their taxes and Homer says, "I was an astronaut!" The salesman doesn't believe him, but Homer was actually an astronaut during the episode "Deep Space Homer."
In Matt Groening's other show Futurama Bender calls himself Mr. X so he won't be killed by the mafia.
In this episode Homer spreads gossip on Springfield's denizens. Such gossip was previously spread in "Wild Barts Can't Be Broken," where it was suggested the gossip gets posted on the internet. However in "Wild Barts Can't Be Broken" it was revealed that Homer had a lot of secrets, making him hypocritical.
Homer's doppelganger is speaking with a german accent. For the german version of the episode, it was changed to resemble an italian accent.
Near the new pool, there is a guy with the words "City Worker" on the back of his blue shirt putting finishing touches on a statue. He is using cement from a bag labeled POTHOLE CEMENT. Later, when we see people repairing the pothole, they are wearing orange jump suits, and the stuff they are filling the hole with is most definitely tar.
When Homer enters his URL to show the family his page, all the keys he types are function keys, control keys, and numeric keypad keys—but no letters.
When Homer has the computer in the kitchen it has a can holder and other features. But when he is using it on the sofa it has none of those features on it.
Lisa was shown to own a computer with internet connection in "A Tale of Two Springfields," where she looks up a website called whatbadgerseat.com. Also in Das Bus, Homer ran an internet company despite not knowing that the Internet exists on computers in this episode.
Potholes are actually treated with a 'Cold' or 'Hot' mix, depending on the season, which it's a asphalt-based mixture, not cement.
The woman presenting the Pulitzer never mentioned the category in which Homer won the prize.