Man...I recently picked up GTA V again (I know it's not retro but hear me out). And when I sit back and think about it, that series has to be top 3 all-time. As a child, when I played most of the games mentioned in this thread, I can vividly remember having the discussions "they need to make a game that does
x" or "what if you could do
y in a game". Rockstar basically took those imagined thoughts and exceeded them, by FAR.
Sorry for getting sentimental fellas
On a related note, were any of the GTA knock-off games any good?
Simpsons: Hit & Run was superb, but I never paid attention to the others.