What would your picks be?
I'd go with:
Easy Rider (1969)--hippie drug culture
Saturday Night Fever (1977)--disco, duh
Fast Times at Ridgemont High (1982)--Only a handful of hits, but seems to have the real feel of the early 80's
Footloose (1984)--80's cheese
Top Gun (1986)--more 80's cheese
Singles (1992)--With the exception of Nirvana, all the major grunge bands are here, along with some alt.rockers of the time. Has a very early, dawn of the grunge/alt. rock feel. I absolutely love this album.
Reality Bites (1994)--Nice mix of 90's college/alt. rock
The Crow (1994)--Good mix of industrial/grunge from the early/mid 90's.
End of Days (1999)--Not very good, but definitely, very 1999. Limp Bizkit, Creed, Powerman 500, etc.
Once Upon a Time in Hollywood (2019)--Gives you the feeling that you're listening to rock radio on some shitty car stereo in 1969. Great soundtrack without all the usual suspects.