1st: Winning Eleven 4 (PSX)
Altough i think that every new WE is better than its previous, we4 was simply the game i played most in my life. From 1999 untill 2004, when we7 for pc came out. I had a neighbor that in one year we played thousands of Nigeria-Brazil games. And for single player, it had the wonderful Master League.
2nd: International Superstar Soccer and Top Gear (SNES)
That's two games, but take this as a SNES tribute.
I first met ISS in a gamehouse wich had 4 arcades, all of them with this game. Many kids playing, watching, waiting their time, that incredible GOOOOAL scream. Then when i won my snes, ISS was guarantee of good times with friends.
As was Top Gear, the best 2-player racing game ever. The song from the first race is absolutely classic!
Super Mario World, Bomberman 3, Donkey Kong Country, Super Street Fighter II... all great games.
3rd: GTA: San Andreas (PC)
This game has a great atmosphere, the gangs, the cities, you really get to the soul of CJ.
at 4th place i'd place the Championship Manager series, mainly 00/01.