If you're into racing games, 4 of the greatest of all time all came out in 19991 on the PS1.
Ridge Racer 4 You know it, you love it. Game with immaculate vibes, superb art style in both 2 and 3 dimensions, and a soundtrack that has held up arguably better than the game. The little storylines are sick, but in order to get everything in the game it gets ultra repetitive. Non completionists will have a much better time.
Wipeout 3 Easily on the same tier as R4 in every visual way, just taking a different approach. Much different gameplay and a hell of a lot harder. Has some big region/version differences in the details but none of them seem particularly bad. If R4 is the kind of game you chill out to, WO3 is the game you get completely zoned in during. All plot is relegated to the manual.
Gran Turismo 2 I'm not a big GT person so I can't say a lot about this but it's generally held in very high regard. Probably the most well known of the four?
Racing Lagoon Much different than the rest of these games but easily just as good. Trades off a bit in graphics quality in return for an amazing JRPG-esque story. One of those rare cases where somehow no one has really done anything like it before or since, and it was very good.
If you're into big PS1 aesthetics or old racing games, you're doing yourself a disservice not to try them all out.
Feel free to use this as a basis for a very longform explanation and justification as to why they're all some of the best of all time. I do genuinely believe they're all up there and the fact that they all happened on the same console at around the same time is incredible.
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R4 came out at the end of 1998 in japan but it got released everywhere else in 1999 so I'm calling that close enough.