Unfortunately, Philosophy of Time Travel, SoulKerfuffle, and the LBAM all generally agreed on the top adventure games, mostly because all smart people (obviously, including your Omnipotent Blogging Triumvirate) agree by consensus that the Adventure Game attained perfection sometime between 1989 and 1992.
Fortunately, the LBAM's intellect dwarfs that of his esteemed companions* and so he is prepared to club them into mewling submission with his discussion of strategy/simulation games.
Without further ado, the greatest Simulation/Strategy Games Ever
5. War in Middle Earth - Talk about kicking it old school. This baby was released in 1988 (random thought: oh Sweet Holy Christ, that was 20 motherfu&^ing years ago and I remember it with clarity. I am practically the undead) and was definitely the first glimpse I ever got at a real-time strategy game, and even better it was set, obviously, in Middle Earth! What more could a budding gamer geek have asked for? This was the entire War of the Ring in one game; you started with control of the Hobbits out in the Shire, Theodred and his Eored of 120 cavalry, and Faramir with 200 rangers. Come too close to an enemy with troops, and the balloon went up. Believe me, there was nothing sending you scrambling for the "restart" option like brushing past Minas Morgul with Faramir while sending him to go retrieve something and watching 10,000 Orcs, the Corsairs, the Haradrim, the Easterlings, and a few hundred Olog-Hai suddenly marching on Minas Tirith, with only the Tower Guard and a hundred knights or too in place. No Rohirrim, no muster of Gondor...truly, it was pants-crappingly terrifying. Especially considering that this could happen while Frodo and the Ring were still in Hobbiton.
Anyway, this was a great game, very complex, everything that is in the books is in the game; Bombadil, Radagast, the Barrow Wights, the Grey Company...everything. Not to mention the fact that besides the War in Rohan and Gondor, you had to manage attacks by Sauron's forces in Lorien and Erebor. The entire map of Middle Earth was open to you, and there were encounters and treasures to be had all over. Just a great game, especially considering the era it debuted.
4. Covert Action - Best spy game ever; quite possibly the only spy game I ever played, but nonetheless, this game had it all as a spy game; wiretaps, car chases, cryptography, breaking and entering, then checking out hot babes at the end. Depending on how your mission turned out, you could regale the, uh, local talent at the laundromat with tales of your badass spyhood, or entertain bikini-clad chicks on the beach, lovingly rendered in beautiful, 16-color VGA. God bless the early 90s.
3. Warlords - We've all played it. We've all played it for 14 hours straight, most likely, perhaps only interrupted by meals. Definitely one of the granddaddies of the turn-based strategy genre on the PC, the game had almost endless replay value given the different factions and difficulty levels. Great game.
2. Master of Orion - You can keep your "Starcraft" and other nonsense. I'll be over here, playing the real sci-fi strategy game, kicking ass, taking names, and sucking your fleet into nothingness with my black-hole generators as the Psilons. Seriously, was there anything cooler than being able to design your own starships, from snub-fighters to huge cruisers, mixing armor, shields, weapons, maneuverability, computers, and special systems? What a huge geek I was; I would pick a 'theme' of names for my starships, like, say, celestial phenomena (Nova, Corona, etc) and then, the first cruiser I built would be the "Nova" class, or whatever, and the first upgrade was "Nova II," then "Nova III" and so on. Yeah. Geek.
1. Wing Commander II - What a great game. Best space combat ever. There were some elements of the original Wing Commander that were probably better, but this had a great storyline, especially considering how it changed depending on how successfully you pulled off your missions. That particular feature is what keeps this game on the list and the X-Wing series games off of it; it was stupid that you had to complete a mission perfectly in order to advance to the next one. Among my finest moments; taking out a Kilrathi supply ship using the crappiest ship, which, if I recall correctly, was the Ferret.
Honorable Mentions: Star Wars: Rebellion, X-Wing, TIE Fighter, Wing Commander, Wing Commander: Armada, Jagged Alliance, Earthsiege, Battle of Britain...I could go on and on. Why, exactly, did we put Sim and Strategy games together? Whose idea was that? PoTT, I'm lookin' at you...
Edit: Worst Strategy Game Ever - Dwarf Fortress - There isn't enough wtf to decry this game with. I mean come on. If you're going to expect me to care about the lives smelly, hairy little dwarves lead, at least have the decency to present them in some way that doesn't make me cross-eyed. I gave up trying to decipher awful ascii graphics when I was 8. I suppose if you're pining for 1982 and your old Amiga, you might find some nostalgia benefit from this heap of crap. Otherwise, you're just wasting your time. why the hell should I care what a bunch of little @ signs do? I don't. You can't make me. Sorry, but games that are in the gutter looking up at Tron for advice on graphics and presentation get no love from me.
*Excluding the following fields; computer programming, understanding of financial systems, environmental engineering, math of absolutely any kind, systems engineering, playing internet poker, not throwing up at weddings, totally, massively, and unrepentantly twinking out D&D characters.