Best Sim is Grand Prix Legends hands down, good luck finding it though. Lately there haven't been any really good sims though ever since EA grabbed up everything they could find. F1 2003 is supposed to be really good and it has some good mods for too.
Just for fun though, Project Gotham 2 if you have an Xbox, Haven't tried Rallisport 2 for Xbox, but 1 was good, and 1 is 20 bucks if you can find it.
IndyCar Series 2005 just got released today for XBox. Supposed to be pretty good, and codemasters has been doing a fairly decent job with racing games as of late. 12 player MP on LIVE too. I think I may pick it up.
Actually, while we are on the subject of racing games, anyone use any of the wheels for the XBox? I'm looking to pick one up and was wondering if anyone had used them. My only requirement is that it has paddles on the back I can use for throttle and brake because I despise the foot pedals on all racing wheels.
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Just for fun though, Project Gotham 2 if you have an Xbox, Haven't tried Rallisport 2 for Xbox, but 1 was good, and 1 is 20 bucks if you can find it.