Well I don't know about Windows '95 (maybe the first Age of Empires, HyperBlade, Krazy Ivan, Dark Earth, Rocket Jockey, or SimCopter)
but I'd love to see Starshot: Space Circus again. It was one of the first games that required a Voodoo 3dfx card in order to play. That, Forsaken and Star Wars: Rogue Squadron. Unfortunately no one has managed to make Starshot playable again.
And what about UBIK? From what I can remember it was W95 compatible. Too bad they didn't make it like in the trailer (natural character movement and all that). The final game came with a lot of bugs... so many that I don't think there was a system capable of playing it right.
Or perhaps X Files: The Game. If you can bypass it's need to install Quick Time the game itself is a gem.
I have a version of Bad Mojo (the original one, not the Redux) that goes through DosBox and it doesn't require Quick Time like it used to. Maybe there is hope for X Files too!