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For racing games, how's about some old school arcade Sega PC titles like Sega Rally Championship 1 and 2, Sega Touring Car Championship, Daytona USA Deluxe, Manx TT SuperBike, or their own version of a Gran Turismo-type game, Sega GT.

An here's a classic EA one, Road Rash, and of course the earlier Need For Speed titles.
 
I went into town the other day and thoroughly enjoyed myself going into charity shops or 2nd hand shops looking for ps1 games. You are bound to find a few you liked at £1-2 each :-). I got street racer.and micro maniacs for a quid each. One charity shop had a mint tomb raider 2 PC for £1.
 
Looks like you've played the majority of well known good games from that era already. You mentioned Freespace but not Freespace 2; if you haven't played it then I would heartily recommend it (probably the best non-FPS game of the last millenium).
 
Serious sam, castle wolfenstien, no one lives forever 1&2, soldier of fortune. Sorry in advance if these have been already metioned as i was too lazy to read the whole thread
 
download mame,might be very early 90's late 80's but top games i like to play are final fight,streets of rage 1,2,3 the original mortal combat,robocop:D

old but still great games,remember playing them in the arcades?? hehe
 
quake 2
quake 3
the secret of monkey island
monkey island lechucks revenge
painkiller
farcry (might run)
ut99
 
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Vampire Masquerade Redemption - surprised no one has mentioned this yet!
Half Life + Blue Shift, Opposing Forces etc
AvP - The original and best, not those terrible "sequels"
Kingpin
Starcraft
Max Payne 1 & 2
Settlers
Carmageddon
Unreal Tournament
Project IGI
Jedi Knight + sequels
Soldier of Fortune
Simon the Sorcerer 1 & 2
 
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