I'll give this a guess...
1. Clinton/Nypro in 1992
2. Definitely 1999, I know that for a fact. My guess on the other game would be 1996, cause I know Andy was our human player and I think you could acheive a high score that year.
3. American Adventure. With the FIRST Cheerleaders.
Good idea Andy! It's fun riding in the way back machine.
(PS Andy- I notice your picture with the 3-finger willy machine. I bet I can beat you at it :-P
)