I’m so sucking and low player that actually for past fifteen (!) years I’ve been playing in actually four games: Diablo I, Diablo II, Civilisation and Transport Tycoon. The first two caught my heart so deeply that I even try to run them (Diablo I!) on Windows 7. And… I actually managed to do this.
Since, this involved a lot of googling and asking, here is a summary of my findings.