UPDATE (18 Sep 2011): Xskreblin (see comments) has found something that might solve this once and for all: the Microsoft Application Compatibility Toolkit. This seems like it might be the final answer to all 32 bit application compatibility issues.
IMPORTANT NOTE: This solution, whilst easy, only works for 64 bit VISTA. If you have 64 bit XP, and work out how to fix it, please leave a comment telling us what the solution is!
UPDATE: 64 bit XP users, I *may* have found a solution: download the file from here, and replace the hw.dll file in your HL directory with it. It doesn’t fix Vista 64, use the method below for that, but I have no way of testing XP 64 to see if it really works. File is from here, I didn’t make it, so don’t blame me if it breaks your computer [and Dice of Doom accept no responsibility for the file either
ed]. No matter whether it works or not, please leave a comment telling us the result!
So, I got a new laptop recently, with Vista 64 bit, required because 32 bit can’t handle the 4GB of RAM I’ve got, and I installed HL1; tried to run it. Guess what happened?

Wait, what? I have NEGATIVE RAM!!! High five, guys!
The problem is not actually Windows Vista, or the 64 bit system itself… it’s just how 32 bit applications interact with 64 bit stuff, namely the memory addressing. For the record, I like Vista: if you have a computer forged by Dwarves in the mines of Moria (which both my desktop and laptop are) then it runs fine, and I like the new stuff it brings to the OS. Aaanyway… back to the issue at hand.
Fortunately, the problem is pretty easy to solve. Right-click on the icon, click Properties, go to Compatability, and set it for XP SP2. For some reason this gives the program only what RAM a 32 bit application can handle (even though there’s 64 bit XP), and it solves the problem. Yay! Pretty wierd, though.

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