Personally I’d go with Independence Day if I had to pick a movie that felt the most 90s.
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.
The Matrix was basically 2000’s. It’s a 90’s movie only a technicality; it was released to theaters in early 1999 and the home release was in May of '99. However, going into the 1999 -> 2000 holiday season the presence of that movie in particular on disc sold a lot of DVD players and Playstation 2’s.
Y2K or thereabouts is precisely when a lot of people experienced the first Matrix.
