Top 5/10 whatever, I always like these topics because it gives me the chance to make others learn about excellent games lost in time/knowledge/market/etc.
Well, I usually list them by type:
RPGs:
1. Darklands (PC)
2. Ultima IV: Quest of the Avatar (PC, ATARI 8-bit)
3. Ultima Underworld: The Stygian Abyss (PC)
4. Sentinel Worlds I: Future Magic (PC)
5. Dragonstomper (ATARI 2600)
Honorable mentions: Phantasie (PC, ATARI 8-bit), Betrayal at Krondor (PC)
Adventure:
1. Monkey Island (PC)
2. Dallas Quest (ATARI 8-bit)
3. Asylum (ATARI 8-bit)
4. King's Quest IV: The Perils of Rosella (PC)
5. Heart of China (PC)
Strategy:
1. Master of Magic (PC)
2. Civilization (PC)
3. Colonization (PC)
4. Heroes of Might and Magic (PC)
5. War Inc. (PC)
Puzzle:
1. Fool's Errand
2. The Incredible Machine
3. Realm of Impossibilities (ATARI 8-bit)
4.
Hybrid (like RTS, Action RPGs, etc)
1. Majesty (PC)
2. Dune 2: The Building of a Dynasty (PC)
3. Darkstone (PC)
4.
Simulation:
1. Wing Commander 2 (PC)
2. Wing Commander (PC)
3. Privateer 2 (PC)
4. Red Baron (PC)
5. Falcon 3.0 (PC)
Sports:
1. Micro League Baseball (ATARI 8-bit)
2. Earl Weaver Baseball (PC)
3. Hardball (PC)
4. Front Page Sports Football (PC)
5. TV Sports Basketball (PC)
Racing:
1. The Great American Cross-Country Road Race (ATARI 8-bit)
2. Poleposition (ATARI 8-bit)
3. Stunts (PC)
4. Racing Construction Set (ATARI 8-bit)
5. Pitstop II (ATARI 8-bit)
Platformer:
1. Flashback (PC)
2. Another World (PC)
3. Montezuma's Revenge (ATARI 8-bit)
4. Spelunker (ATARI 8-bit)
Sandbox:
1. Populous (PC)
2. Populous 2 (PC)
3. Populous: The Beginning (PC)
4. Sandbox God (PC)
Well, that's what I can think of, so far.
As you can see, no NES, SNES, Genesis, N64, XBOX, PS games have been listed because I went from ATARI 2600 to ATARI 5200 to Colecovision to ATARI 8-bit to PC and stayed with PC.
No, I'm not a dinosaur. I just started early.
This might change over time as I remember more games :)