Its kinda hard as some of the games im going to list really made its mark for me for the online multiplayer part. But had great single player also.
1)Total Annihilation 1997( was an RTS way ahead of its time,, downloadedable units for one, 3d terrain, being able to set units to patrol area's. Its universe worked well for multiplayer which is a detail that always bugs me, its never ending war, so makes sense for online gameplay. keep an eye on Planetary Annihilation, same guys)
2)Dungeon Keeper 2 1999 (being bad is good i think was the phrase they used. It was great playing the bad guy taking care of your creatures and deamons like little evil cyberpets before you go and invade the goody goody dungeon, had a great sense of humour)
3)Half-Life series (just still a great fps, i know its overstated but prob set the standard for FPS today, and single player story great, just STILL waiting for a conclusion almost a fucking decade on)
4)Counter-Strike 1.6/CS:S&CS:GO (there is a reason why its still one of the most played fps games ever to this day and it first came out in 1999, so much fun and satisfaction, some great fire fights and endless user created content)
5)Dawn of War series (One of the only games to do the warhammer 40k universe justice in a video game, capturing the atmosphere best ive seen, and a kick ass RTS with a new spin, no more base building and more focus on getting in the action. Its hard to master but when you do, its epic.sadly not as popular as the likes of StarCraft)
6)Doom 2 (every gamer should play single as, or hand in your gamer card, if for nothing else to see how it all started)
7)Portal 1&2 (just really surprisingly fun and funny puzzle game, with links to the Half-life universe)
8) MetalSlug series (all round best fun side shooter ever for me)
9)Zelda Link to the past/Ocarina of time (to me they are the same game just one is in 3d. Both have 3 main dungeons/temples to deal with before getting the mastersword and the dark world
either way both legends)
10)super mario allstars+mario world (simply unbeatable classics)
11) Left 4 Dead (just great co-op zombies, hordes of them plus the other infected it really gets the panic factor going alot of fun. I still find this alot of fun as you cant be a hero and solo, you need teamwork)
12)Aliens vs Predator 1999 (the sounds, the looks, the feel, they got it perfect. The marine felt perfect, the guns all sounded and felt powerful the motion tracker added the sense of unease if your team of marines were facing a really good alien hangin from the ceiling or walls waiting to jump on ya or pred player all invisable picking you off one by one. the last thing i heard alot of the whine of the disc before i died. Or the last stand AI aliens vs marines fun fun fun)
13) TeamFortress Classic & 2 ( TFC satisfied the itch of more explosions and heavier guns that CS 1.6 at the time did not fill, boy was that crazy with the nades every class had. While they took out the nades for TF2 the lovable art style and gameplay is pure fun, like being in your own violent pixar movie with body parts flying about. And the MANN VS MACHINE mode is also sooooo much fun)
Command & Conquer Tiberium Dawn,Sun. Red Alert 1( classics, it all went abit silly after EA took over WEstwood and i myself lost interest but i always had fun tank rushing)
StarCraft ( while i hate the series now as SC2 feels just like the SC i used ti play non stop back in the day just with a new lick of paint. SC1 was alot of fun and perfectly balanced. Just get ready to click click click click as fast as you can if you wanna win on multiplayer)
The Sims (really not a game i would play but.....it drags you in, you start off with a power trip being an evil god to your sims, then you find yourself giving a dam about them, then you get the money cheat, then you buy a bunch of shit and kit out a house, then you build a huge house, then you gotta make yourself as a sim and then your friends and then build all your friends homes and kit them out, and then you start trying to get your Sim version of you to WHOO HOO in the hottub the chick friend or girl your know that you semi creeply made into a sim. And then you look at the time and its fucking 3am WTF !?!!?!?! lol