My list
Doom - The first three episodes are infinitely replayable.
Bioshock - A reminder that games are still a great medium for storytelling.
Vampire the Masquerade Bloodlines - Lovingly crafted contemporary horror RPG. Troika was just hitting their stride here.
Counter-Strike - The most addictive MP FPS I've had the pleasure of playing next to MP_SHOP.
Blade Runner - As relevant to the franchise as the movie or novel.
The Elder Scrolls IV: Oblivion - There's enough to keep most people busy for at least 50 hours.
Grand Theft Auto III - High res. High FPS. Mouse aim.
Half-Life - No explanation.
Half-Life 2 - I still prefer the original, but the game is impressive compared to most FPS.
Mafia - Classic.
SWAT 4 - Genre-defining.
World of Warcraft - Like Oblivion, you may retroactively deny its charm, but the game will keep you busy for hours upon hours.
Doom III - Call the game cheap, it's effective at what it tries to do. Nice tech and voice work.
Quake II - And then there were rail guns.
Portal - Incredible. (but we really don't need a sequel. move on, guys)
The Secret of Monkey Island - Ron Gilbert's masterwork.
Deus Ex - I haven't finished this one yet, but it stays on the list.
Leisure Suit Larry in the Land of the Lounge Lizards - Pushing the boundaries of good taste. Encourages safe sex.
Hitman: Blood Money - Still not sure which is the best in the series, but the interface is certainly most polished here.
The Dig - Another fine example of sci-fi storytelling done right.
Max Payne - Bullet time. Noir. Constipation face.
Diablo II - Loot. Still kinda playable. Always memorable.
Indiana Jones and the Fate of Atlantis - Great storytelling and dialogue. Voice work is a mixed bag, though.
(Reserved for Fallout 3)
(Reserved for Alan Wake)
There are still some PC games I wish I'd played, including Fallout 1/2, Wastelands, System Shock 1/2, STALKER, The Witcher and a few others I cant think of.