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Midnight Club II. Agreed that it's hard as hell (I never beat it... 80% or so done), but I really enjoyed it. Also, once you get to Paris and get a fast motorcycle, playing online with your friends and seeing who can jump the furthest over the Louvre... ah, beautiful.
I like the Gran Turismo series for realism. Overall I think they're pretty enjoyable.
There was another I enjoyed, though I can't recall the name of it offhand... a rally game, made pretty recently, for X-Box I think. Interesting because the racing is so drastically different from road racing.
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