On the day of this episode's premiere, the Soviet Union officially dissolved.
Homer is correct about the dark horse candidacy of John Anderson in 1980. However, his comment about the hits of Supertramp is slightly off, as 1980 marked as only the beginning of the decline in the group. 1982 was the big fall for the group. To give the episode flavor about Homer's youth and the timeframe, the band's famous song, The Logical Song is playing when the flashback begins and Homer is seen working at Sir Putt a Lot's Miniature Golf Course. The Logical Song was composed in 1978, and released in June 1979, not 1980, but still retained popularity in 1980 due to Supertramp's tour for their best selling album, Breakfast in America, which was going on in 1980, and the last singles off of the 1979 Breakfast in America album were released in 1980.
The people waiting in line's annoyed reactions to Homer's obliviously spoiling the major plot twist regarding Vader being Luke Skywalker's father was a reference to the fact that the plot twist was kept under strict secrecy during development of the film.
When Homer is seen working at various short-lived jobs to find the right one to finance his married life, most of them are accompanied Dolly Parton's hit song 9 to 5.
Marge's hair is not as tall in this episode as it normally is shown. Presumably her hair is shorter so there is less to wear in her famous updo.
This has been the only episode so far where Jacqueline Bouvier has smoked. It is very likely she has quit smoking.
Mr. Burns is playing a Ms. Pac Man arcade cabinet in his office.
The eye pupils are much bigger than they usually are.
Homer going door-to-door selling knives were a reference to Cutco, which manufactured a brand of kitchen knives which got sold by mail order. Most sales were made by young people looking to gain experience.
This episode aired on December 26, 1991 (Boxing Day), making it one of only two episodes to date to air over Christmas.
After Homer takes the job of safety inspector, Mr. Burns says he will "remember that name," but he wouldn't whatsoever. This could foreshadow a familiar situation in Who Shot Mr. Burns.
At the end of the episode, when Homer tells the kids what a blessing they are, Maggie's bow is missing in one shot.
When Homer and March are leaving the theater after seeing the Empire Strikes Back, the Imperial March (Darth Vader's theme music) can he heard playing. They presumably left the theater when the credits began rolling, but the Imperial March cannot be heard in the end credits until about half way through the credits roll.