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Ridge Racer Type 4 (PS1) has a horribly grind system for collecting all cars, which relates to how you basically have only one game mode where you always play the same 8 tracks with 7 opponents, starting last. Repeat 200 times (getting every possible result with every available vehicle) to get the cool Pacman car.
But it was also one of the most enjoyable driving games of the many I've played.

There would be many games I played once, enjoyed for some reason, but hated certain parts.
Mafia 1 (original) had much great, but FPS parts were awful.
Nocturne is a nicely atmospheric horror game with terrible gameplay.
Betrayal in Antara is more a nostalgia piece for me, but it had its moments. (And I don't mind the graphics, even it was said to be ugly and aged already when it came out.)

Wing Commander: Privateer I've played number of times and that really among games I love. But the fully linear story - where it's game over if you ever fail a story mission - is a big flaw (even if that's how it often goes with generally "open world" games).