My situation sounds very similar to yours. I started out with a Commodore Vic20. The upgraded to a C64 with a tape deck! Then an Amiga 500 and even an Amiga 2000 when I was in college. I didn't get my first PC based system until around 1993. It was a i486-66. Some of my favorites were:
Vic 20: Gorf, Kickman, Omega Race
C64: Forbidden Forest, Castle Wolfenstein, Summer Games, Defender of the Crown, MULE, Blue Max, Bruce Lee
Amiga: Sword of Sodan, Three Stooges,...