UltimaVII: Had a requirement of both high free memory but used its own memory manager, so you always needed a boot disk or a special boot configuration to run it. In hindsight, these requirements weren't that steep, but mouse drivers in particular at the time were real memory hogs. Using a boot disk was more a hassle than a real burden.
A lot of early 90s DOS games can be frustrating to get working just because of how much conventional RAM they want.
I think X-Wing was one of the most troublesome for me (if you want sound fully working, which also requires EMS).
Ultima 6? - When I tried to run this on my last DOS build, the AdLib sound (on an OPL3 Sound Blaster clone) was a painful explosion of noise. Maybe that's a speed issue, I didn't look into it enough to solve it.
Ultima Underworld - If you want Sound Blaster Pro music to play correctly, you need a dual OPL2 card. Otherwise the mixing levels of the different instruments is all whacked. I immediately noticed this when I upgraded to an AWE32 back in the day, and the same issue is present in every Youtube video. A lot of people don't seem to notice if they've never played it on the card it was programmed for.
May sound weird but back in my 386 days had trouble getting Magic Carpet to work smooth with good audio. Yeah was recommended for 486 but did not have one yet and remember finally getting it to run smooth and then lost interest. That and one other game back then but it's name eludes me for now...
Also very picky when it comes to sound. I had to downgrade to SB 1.0 replica to get DA working at all, despite my other cards (both SB16 and some otherwise bulletproof Aztech SBPro2 clones) working in everything else I could throw at them.
Not a speed issue. I have it on my UMC U5S-33 system, but not on a K6-2 350. It's only AdLib - I can do SSI-2001, CMS, MT-32; everything else works fine, just not AdLib. Also haven't looked too deeply as U6 will run on so many other systems anyway without the issue.
This isn't the same. That other thread is I can't get these games to run on windows 10. This thread is more about difficult games to get running on period correct or even older systems that should run it.
rise of the triad in its original release to my knowledge still hasn't been cured from the mid 90s shooter plague that is player movement mapped to mouse y-axis, at least the different iterations of NOVERT don't have any effect.
jazz jackrabbit 2 has always had rather jerky scrolling that also hasn't been addressed in recent fanmade patches, regardless of hardware. they got the scrolling right before with JJ1 but apparently doing this kind of game for windows came with different challenges. should also be noted that only software mode gives the full graphical featureset here.
master of orion 2's fan patches have always been targeting the multiplayer DOS version community only, which is unfortunate as that version apparently forces mouse acceleration on for whatever reason. between this and the pointless black transitions that this version has when switching between a planet and the galaxy screen, i'm one of the seemingly few that prefer the win95 version, even though it certainly comes with its own list of flaws, such as the good old "mark block stack size" crash (which is supposedly related to a memory leak).
diablo 2 can really be a stutterfest on win98 with period hardware (read: HDDs) due to how inefficiently the game loads in assets on the fly while running around on the map. despite this, the game still manages to be a RAM hog for the time, easily using 128 mb of physical memory after 10-20 minutes of play, and that number will only grow as more stuff is cached in. there's a number of threads from back in the day with people complaining about this, plus poor performance in D3D mode.
I don't know any games "difficult to get working" in the sense they were difficult to run with most configs for specific games problem even if some probably had problems. I suppose it depends on the "common" config of the specific era.
Instead games that were heavy with most most common config, I'd say for myself Wolf3D, Doom 1 & 2, Quake obviously, Thief 2 but one game that make me sad was Stalker.. I remember having just upgraded my (last) modern PC in the 2005/6 probably, an Athlon 64 3500 with a X1800XL vga and bought that game cause it seems like they talked good about it and even if the system were not a slow config, the game ran awfully slow and unplayable at high details even low res even if I actually spent a lot on those system components coming from a XP 3200+ and a Radeon 9500 Pro modded.
After that I never built again a modern config. I sold every of those components and switched to notebook and left pc modern games forever. It happens from time to time to build Core2 systems as the most modern ones for Linux but I completely lost all the evolution from 2005 to 2020 on desktop. The most powerful config I actually have is a Core2 E8600/DDR3 mobo, the most modern VGA I have got is a GT610 1GB DDR3. My everyday home office machine is a mini-itx Atom based pc. ?
Duke Nukem 3D - Used to have an AWFUL time getting music to work on this game in DOS or Win9x DOS Window because for some weird reason it would not find my MIDI hardware on an old IBM PC-330 486 with an ESS1869 (IO Magic MagicSound 16) sound card in it. That sound card itself was a pain in Windows 9x anyway because the IBM would automatically set it's memory address out of range of DOS causing it not to work in DOS Mode.
The Secret of Monkey Island - on older SoundBlaster Pro 2.0 and compatible cards there was a flaw with the 1990 VGA floppy version on faster computers. I used to be able to find the update somewhere online but I can't remember where I got it.
Ultima VII Parts 1 & 2 in pure DOS always require a special configuration to work, one that frees up as much base memory as possible - I usually only load HIMEM.SYS and the Mouse Driver and rely on hardware detection for the sound hardware to save the 574K or however much is needed.
For Windows, NASCAR 2 crashes when booting up the CD-ROM to install it in Windows 98 or higher, but works fine on 95. I think there's a few other Sierra Titles I've had that problem with as well that I recently got (they're titles that are soft of like Myst - but Myst gives me no problems with anything). I also have old Softwrap installs of Postal and Postal 2 I had to delete because S***wrap (SoftWrap) ended (good riddance) a long time ago.
Some of the games made for Windows 3.x are a bit annoying because they either expect 16 or 256 color modes, and almost everything I have that's not a 286 or older can do 16-bit, 24-bit, or even 32-bit color so they usually live in that world. Sim City and Sim City 2000 are a minor annoyance with a few artifacts, but the big killer are the Sierra graphical adventure games (Leisure Suit Larry 5 and 6, and Freddy Pharkas to name a few) which at any mode above 256 color will just black out most of the screen assets except buttons and other functional bits of the game, but backgrounds and characters are invisible.
That said there are some games that will (almost) run on anything. I got Diablo to start it's installation in Windows 3.11 For Workgroups (I'm assuming under Win32s), ad that game also runs on Windows 10 IIRC (have njot tried in awhile). My 486's run Quake comfortably enough but the Windows version has a pretty wide swath as well. Same with DOOM. Ultima VII actually run GREAT under Windows 9x using U7dpmi and U8run for Pagan (Ultima ? and they still run on their suggested hardware fine that way.
I'm a bit surprised people have had trouble with Ultima VI - I found my only problem was I was setting it up for Creative Labs GameBlaster (totally different froma SoundBlaster) instead of Adlib (out of my ignorance at the time, it was 2001 when I was doing that). Though I recall that being a problem on one card I had (I think it was a Reveal Crystal chipset card on an old 486 I had years ago). I've got U6 running on everything from my Tandy 1000A (very slow) to my modern systems under DOSBOX.....I usually use that game to display the actual power of the computer it's being run on. Shoot, 8088, 286, 386, 486, Pentium, DOSBOX, Nuvie.....I'd think out of all the DOS games ever made U6 is the one you can trust to run on anything.
I was surprised too. Assuming you don't mess up card resource settings (not a game problem IMHO) it's run perfectly on every system I've played it on, from my mum's PS/2 70 in 1990 via my own first P60 in 1995 to my first retro PC K6-2 350. It only started playing up - and then only in AdLib - when I moved my main DOS system from P200MMX to U5S-33, in an attempt to get U7 (which is a timing-sensitive PITA as well as a resource hog) working correctly.
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