It isn't a movie itself, but the "work sucks" genre of films had its peak in the 90's, specifically 1999.
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Do the Right Thing - Spike Lee
Prep for the 90s.
This isn't the most quintessential 90's movie, or even a good movie, but the fever dream of Romeo+Juliet (1996) is the most 90's thing I've ever seen in my life.
The Birdcage and Get Shorty are tied for me
Crimson Tide
PCU
It's funny, at the time we probably would've said Reality Bites.
Aliens/Alien3
American Pie or My Big Fat Greek Wedding.