gris (artsy 2d platformer with light puzzle elements)
if on a winter's night, four travelers (free! short point-and-click adventure game with horror elements and a heavy emphasis on its story)
NaissanceE (free! first-person platformer in a weird liminal space)
post void (weird mind-melting boomer shooter roguelike)
riven: the sequel to myst (brilliant old-school point-and-click adventure, but it also has all of the things that make these games frustrating)
subway midnight (stylish, short horror game)
this war of mine (survival game about being a citizen surviving a war in your country. very stressful and depressing, but in a good way if that is your thing)
@wallhackio too bad steam doesn't run on windows 95