when the diegetic licensed music is of a time but not the right time eg
yellowjackets — set in 1995, features “song 2” (1997) (while in 1995 timeframe)
mgsv — set in 1984, features “friday i’m in love” (1992) and “the final countdown” (1986)
life is strange: before the storm — set in 2010, features “no below” (2013)
in michael mann’s public enemies baby face nelson does a james cagney impression quoting “angels with dirty faces” (1938) right before the shootout at little bohemia (april 1934)
mgs5 also had that trailer that famously used elegia which is from 1985
mafia 3 takes place in 1968 and all the music is period accurate (a great argument for setting your games near the end of a decade) though there are some curiosities like having actual paint it black (1966) and the avengers cover (1983) but they only play the anachronistic one once for effect in a mission. they do this with the misfits version (2003) of you belong with me by the duprees (1962) as well because the game has a 2016 framing device it kinda sorta abandons later on. anyway I wanted to talk about it because very few games put enough care into their soundtrack for that to be noticeable, and also games usually have shit taste in 60s music
on the opposite side there is scarface the world is yours is a non canon sequel to the movie that takes place in 1983, which has maybe the least amount of effort put into this possible. theres a d12 song in that game from 2004, cypress hill, rob zombie… and most of the 80s songs are off the movie soundtrack, off the GTA vice city soundtrack, or from 5 years in the future.