I have a 16:9 ratio monitor and whenever I try to play older games that don't support such ratio's they always end up looking oddly squashed to a nearly perfect square instead of a 4:3 ratio rectangle. Is there any way of fixing this ( besides playing in windowed mode) or am I forever doomed to play this way?

Most monitors today have a 4:3 mode, where it resizes the display to a 4:3 aspect ratio, to simulate resolutions that are not widescreen. They are usualy enabled by the press of a button. Try to test around the buttons on the monitor, or if you're felling unsafe, then find the instruction manual of the monitor, and look for there.

It's even better to use aspect scaling on your graphics card. If your card is NVIDIA, see the attached picture.

Well, I found a very very convenient button on my monitor I never really paid much attention to before. It's the "auto" button which automatically sets the correct aspect and resolution for the current program. Thank goodness for modern conveniences!