Ironically, I had more issues getting old Windows games to run on Windows 8. Several ran with minor glitches, and a couple refused to run at all.
Jagged Alliance 2 is a classic, turn-based tactical combat game in which you lead a band of mercenaries, each with a distinct personality, through the liberation of a fictional Latin American country. The game shipped in 1999 for Windows 95. However, in my tests the version on Good Old Games wouldn't run: When I tried to start the game, the first bit of music fired up, but all I got after that was a black screen and silence. I suspect the issue is more sound- than graphics-related, but the Compatibility Troubleshooter didn't yield any success either.
Kohan: Immortal Sovereigns is an oddly named real-time strategy game. It's an unusual mix. First, you engage in area control, where you take cities by capturing them, which generates more resources. The units you command level up, making them stronger over time. You can customize the units as well, giving them, for example, a generic infantry unit scouting capability. Finally, the "immortal" parts are the heroes, which add more strength and flavor to your armies. No game since has managed to match this clever combination. Unfortunately, though, the game simply refuses to launch under Windows 8.
Age of Wonders 2: The Wizards Throne is a game of exploration and conquest, a kind of lightweight, fantasy version of a Civilization game. The game ran on my Windows 8 system, but the sound would cut out intermittently and the mouse pointer would occasionally fade in and out.
The first Baldur's Gate RPG from Bioware generated a lot of excitement when it initially shipped. First, it was a computer RPG based on the Advanced Dungeons and Dragons 2nd Edition rule set. Second, it offered fully cooperative, six-player parties over local area networks. The sequel, Baldur's Gate II, used the same game engine but upped the resolution to a whopping 800 by 600.
The current version available on Good Old Games runs fine as a single-player game on Windows 8, but multiplayer seems broken. Performance issues also seem to crop up. Despite the fact that it's purely a 2D DirectX game, I was seeing only 25 to 30 frames per second on a high-end, GTX 680 graphics card. It's playable on Windows 8, but the experience isn't as good as it should be.
The rest of the games I tested seemed to run flawlessly.
Roller Coaster Tycoon was one of the first "tycoon" style games. You built a theme park and tried to attract visitors, but you always had a tight budget. It's as much a business sim as it is a strategy game. It achieved a brief notoriety when users started building unfinished roller coasters to see how far they could launch carloads of passengers into the air. The game as delivered from Good Old Games seemed to run fine in Windows 8.
Sid Meier's Alpha Centauri came out not long after Civilization II, and the gameplay is similar. Unlike the Civilization series, however, Alpha Centauri tells a story, and it makes heavy use of its science fiction theme. In a sense, it's a true successor to Civilization II, since the events take place ostensibly after you've launched your starship to Alpha Centauri in Civ II. It's a deep game with brutally effective AI, so you'll need to keep playing to master it.
Freespace 2 is a combat flight simulator set in space. It tried to model physics more accurately than previous space sims did, but that made the game a little harder to play. The game also entailed a lot of huge fleet actions, which tended to make your little fighter seem insignificant. Even so, it was a fabulous title whose gameplay has yet to be replicated. It runs great under Windows 8, and the fact that it takes place in space makes it look a little less dated.
Another Bioware RPG—the one that launched the company into the Star Wars franchise—is Star Wars: Knights of the Old Republic. KOTOR (or SWKOTR), as its fans call it, set up the form and structure for future Bioware RPGs; you can see the influences in current Bioware titles such as the Mass Effect series. Knights of the Old Republic runs smoothly, and looks surprisingly good, on Windows 8. Not bad for a game that shipped nearly a decade ago.
Thief defined a new genre: the first-person sneaking game. You played a thief who received missions that typically involved breaking into mansions or other structures and taking items of value. You were always underpowered relative to the enemies, so engaging in combat was generally a bad idea. You can see a bit of Thief in Dishonored, a recent title from Bethesda, which is no surprise since one of Dishonored's designers was also a designer on the Thief series.
I wasted a huge amount of time on Unreal Tournament 2004 back when it first launched. You could play UT2004 cooperatively or competitively, and it was always a blast. Back in the day, my gaming group much preferred UT2004 to Quake III. The version available on Steam runs without any hitches on Windows 8, and most of the publicly available add-ons work as well.
Not every game I tested ran, and not every game that ran would run well. Still, I'm heartened by how many games did run on Windows 8. DOSBox continues to be a great tool for both end users and publishers, enabling classic, old-school DOS games to find new audiences. Given the "8-bit" trend among some of today's game developers, these games may find an even wider audience than mere nostalgia might indicate.
Older Windows games run for the most part, but not all of them do, and they don't always turn out well. Even some newer games have issues with Windows 8, such as Crysis 2's permanent lock to vertical sync. But if you have an older game that's a favorite, chances are good that you'll still be able to play it today.