Homer’s prank to Moe of unscrewing the sugar canister is a similar prank Bart did to Milhouse with the salt shaker in "Homer Defined".
When Marge told her therapist about her first day of school and how she was teased on the bus about liking the musical group The Monkees, the girl in the seat next to her stated the members of the band didn't write their own songs or play their own instruments. In reality, all four cast members had musical training and either already knew how to play instruments or learned as part of being on the show. In the second season, most of the songs were written and performed by the group. Years later, the analogy was given that it was as if the cast of ER went out and actually became doctors.
One of the bars that Homer visits is the bar from the sitcomCheers. All of the characters are voiced by the actors who played them in Cheers, with the exception of Frasier Crane who remains silent. This is perhaps because Kelsey Grammer has made multiple appearances on The Simpsons as Sideshow Bob, he does not lend his voice to this episode.
At the end of Homer's visit to this bar, a few notes from the end of the Cheers theme song, "Where Everybody Knows Your Name", can be heard.
Grampa being left on a plane and proceeding to slap his hands on his face and yell is a reference to the movieHome Alone.
The films Homer rents areHero, Fearless, and Alive, the latter of which Marge watches. All of them involve plane crashes.