Factual error: The shop owner shows him a tape of the Joshua Tree by U2 and says it is the best concert he has seen, but the Joshua Tree wasn't released until 1987.
Factual error: In the scenes set in 1985, young Bart is using a set of Sony headphones that were not available until 1991.
Continuity mistake: When Bart's dad asks how he got such a beautiful girl, he looks at Bart. The shot cuts to behind him and suddenly he's looking at Shannon again.
Factual error: In the scene in 1985 when Bart's mother takes him into town, they drive by a movie theater. Up on the board it shows two of the movies playing is Goonies, and Jaws 3D. Goonies is right as it came out in 1985, however Jaws 3D was only in theatres in 1983.