Although I very rarely play these days I'd say Counterstrike as it's the game I've put most hours in to and it still as a huge following and is constantly evolving but not so much as to be unrecognisable.
So hard to pick one as there is so many to choose from. When I think back to all the games I've played, these are the ones I only remember and the most fun I had.
Wow (Vanilla)
Deus Ex (Original)
Witcher 3
Outcast (Looking forward to the remake!)
Max Payne
Championship Manager '99
Sensible Soccer
Call Of Duty 1 (MP)
Mafia
Skyrim
Thief 1, 2, 3
Hitman
WoW. No contest really. I've been playing it 11 years. I've tried other games in that periond but and had sank some serious time into games such as the Total War series (Rome 1 and Empire mainly), the Civilization series and a few others. But none have the longevity of WoW. I always go back to it.
In history? Well in sheer number of hours that honour is still held by the original Elite I think though Skyrim may well exceed it at some point. Either way its close.
MP: MOHAA, absolutely freaking loved it. If they decided one day to do a CoD4 re-skin then I would purchase it in an instant, the MP maps on that game were shear perfection. Destroyed Village and V2 were just unbelievably good. I must have spent hours on V2 just hurling grenades through doors then closing them again quickly. Once you broke through the first few sets of doors and could roam the rest of the facility....oh man...what a great, great game. SP was epic too, still is.
Mine would have to be World of Warcraft Vanilla , I pretty much played it everyday on and off for over 3 years ! In its current state I wouldnt touch it , everything I loved got changed or taken out the game but wow would be my all time game because of the amount of time I put in too it and how i would go to work twitching for the day to be over so i could play it , I even had time of work sick to play it lol ! just a little addictive but that is my all time top game.
I will give my 2 pence hear and throw a curve ball and say any Championship Manager up until CM4, if said person wasn't into football I'd say Command & Conquer Red Alert
Deus Ex together with Resident Evil and Final Fantasy 7 are games I most replay. Usually every few years. Most other games do not pull me to revisit them once complete.
For multiplayer, probably DOTA 2 or Age of Empires 3.
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