Factual error: During his interview on K-Chat, B.J. Smith says "Like the song says, 'don't call it a comeback.'" The song he's quoting is "Mama Said Knock You Out" by L.L. Cool J, which wasn't released until four years after the game takes place.
Other mistake: In 'Keep your Friends Close,' in the first cutscene, Tommy says put 20 million in cases, but the subtitles say three.
Trivia: After you cross the bridge to the west island, check the stores carefully. One store is called "Carcer City Mattresses". Carcer City is the city in which the game Manhunt (also released by Rockstar, a year after Vice City) takes place.