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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For not-the-best-90s-movie-but-most-strongly-dated-to-the-90s I'd have to go with You've Got Mail
If someone had told me Independence Day was early 2000s (pre 9/11) I wouldn't have doubted it. Same with the Matrix really.
But You've Got Mail seems rooted to that mid to late 90s early internet feel. Two massive stars. Lots of 90s fashion etc
Possibly also Mrs Doubtfire. Reasons there being very 90s exploration of divorce, prosthetics that weren't available in the 80s and a theme (man sneaking into kids lives in disguise) that I don't think would have gotten traction 2000s onwards for being too creepy. Makes it a very 90s film.
Terminator 2 is in a weird spot since it's a sequel to an 80s movie but is itself a 90s movie. But I'd nominate it for this award.
Space Jam, for sure.
Falling Down (1993), Freeway (1996) are two that I saw fairly recently and the 90's were jumping off the screen.
Pauly Shore had 90's career. Encino Man (1992), Jury Duty (1995), Bio-Dome (1996). His only movie of the 2000's was Pauly Shore is Dead (2003) which was about no one caring about him anymore.
SubUrbia is the 90's distilled for me.
https://www.imdb.com/title/tt0086589/
As for movies from the 90's, Jurassic Park would be my pick, with Forrest Gump a close second, but points docked for not being based wholey in the 90's.
Friday 1995
Wayne's World
Feels leftover 80s to me. Or that weird transition period
When I saw it years later I misunderstood what Wayne meant when, talking of Stacey having bought him a gunrack and being mental, he says "get the net!"
To late 90s me it sounded like he was talking about the internet, sarcastically telling Stacey to "get the internet" as in "be cool, get with the times, stop being a dork"
When pointed out to the me he's referring to the much older trope of catching crazy people with giant butterfly nets, I realised how solidly pre-internet Wayne's World is. And can't be quintessentially 90s for me for that reason.
The Matrix and Jurassic Park come to mind.
Jurassic Park was ahead of it’s time. I don’t really think of it as a 90s movie.
Got Jurassic Park in 4k on my Plex server.
Looks absolutely amazing still.
Can't Hardly Wait.
JLH was unbelievably hot in that movie. that blue shirt and skirt. Whew.
Hit me right in the late teens.
Reality Bites.
Tempted to say The Matrix but it’s late in the decade.
Maybe Scream?
I think The Matrix can work! It feels very 90s to me as well!
It's a 90s movie about the internet, but it's all technobabble magic and represented in a very made-for-TV way. Just the right balance of interesting plot and complete cringe which is pretty much how I remember the 90s.
I’d add Speed. Sandra Bullock was the 90s it actress. And Keanu has already been mentioned in a couple of essential 90s titles.
And you complete the 90s hacker trifecta with Sneakers
God that's such a good movie. Probably gonna throw that on soon since haven't watched it in years.
Can I add Johnny Mnemonic to this list? Classic Keanu
"I NEED to get on-line. I NEED a computer!"
Information Overload! Rollins deserves to be an EGOT.
Gotta double the capacity of the 80 GB drive in my head
"Hack the planet!"