I know it might be a bit of a stretch, but what about running Linux and Wine. It's also free and should work if I'm not mistaken.

Always wanted to play this game. LOL I remember reading horror stories about the disc swapping and some office maze puzzle.

So many games had horrid disc swapping. As much as I love Under a Killing Moon, The Ripper and Black Dahlia...they were all HORRID for that. Still awesome and fun games though...

Black Dahlia wasn't bad in my recollection. Many games were pretty good with keeping chapters of a game separate, instead of having to swap location to location (like Obsidian I think). Gabriel Knight 2 is also great - only a couple times you swap during a chapter, but otherwise one chapter per disc.

Well to be fair, I haven't played Black Dahlia in a very long time so I could probably be misremembering it. Yeah many weren't bad, but some were just horrible. I loved how you had to switch discs half way down the street in UaKM. :P Still an amazing game though.

In case no one has linked to it yet

http://www.gog.com/en/wishlist/games/obsidian

Played it when it originally came out and it was one of my favorite games I'd played back then.

Awesome game, definitely belongs on GOG.

Yes, it belongs on GOG!!!

I bought this back when it came out and it has had great reviews. It was a creative game with a good story and puzzles. I don't maintain old PC's, don't want to bother with VM, and prefer a turnkey solution on my convenient laptop, which has become a desktop replacement. I would love to play this on my Win7 84 bit machine. Obsidian doesn't like 64 bit.

Someone has made a patch for Obsidian for Win 7 64 bit:
http://archive.adventuregamers.com/forums/showthread.php?p=600049 - it is at the SierraHelp site...
HOWEVER that patch may have been polluted by someone else, because it redflags at both virustotal as well as my own scanners as Cloud 9 which (if it is not a false positive, which I don't want to find out personally) is a very tricky nasty trojan, so I chose to not try it - I'm so sad.

So yeah, I wish GOG would be able to license and port this to newer Windows.

Technote for software heads:
I read that Obsidian was made for Windows using mTropolis, which was perhaps the first multimedia authoring tool used in the games and educational software field that effectively and robustly used visually-oriented object technology - reusable, drag & drop elements, libraries, behaviors, all kinds of stuff, plus it was web browser and internet capable. This was bleeding edge stuff in those days. In 1998 mTropolis was acquired but then cancelled in 1999 because the (loudly protesting) user base was not large enough, and Adobe was the big gorilla in market presence & deep pockets in the multimedia authoring field (albeit with a less technically superior product) at the time. Sounds familiar.

Necromungers!

Looks like it's the necro month.

What's worse is that I gave my left one, and I sure as hell didn't get a game for it! :-(

This game is so fascinating, rich and beautiful. It's a surreal haunting experience with little touches of humour reminiscent of Starship Titanic. There's even some goofy FMV sequences, which give this masterpiece bonus points. Get the shovel GOG, please, this old game needs to be exhumed ASAP!
There's a new game at the moment called "Albino Lullaby" that I think was highly influenced by Obsidian.
I have no idea where my discs are for this game, would love to see it on GOG, not just so I can play it but also so that others can experience this beautiful forgotten gem.