I've already told the Contra story about three dozen times in other threads so I won't belabor the point here...that said:
I lived in a group home as a teenager (long story involving a dead father and abusive mom), and there was an SNES in the house rec room. I was a big fan of strategy gaming even then, and Aerobiz Supersonic was my game of choice. It was a bit of a tough sell to the other residents, most of whom were tough kids from the wrong side of somewhere's tracks in Greater Boston, all of them (myself included) troubled teens.
Eventually I got my friend Mike into it, and he got Anthony, then the staff joined in...you get the idea. With a total of 16 people willing to play a 4-player game, we had weekly matches, winner gets to go to the final round.
Anyway, final round came about and it came down to Mike (based in London) and me (based in New York) playing the best game, and we'd divided up about half of the world. I held the Americas and Oceania without much of a challenge, he held Europe, Africa, and the MidEast in a tight grip. Staff member John, based in Tokyo, had a death grip on SE Asia that Mike and I would have to break in order to get the 4th region required for victory, but we were both stuck up against the 40-route limit imposed by the game. We agreed to not engage in destructive competition outside of SE Asia so we were able to strip-mine the less profitable parts of the world to free up routes. Finally the balance tilted: John didn't have enough capital to keep his company running and so lost his airline and dropped from the game - the race was on, and a flight added by me at -50% fare (slash 'n burn at its best) from Hong Kong to Tokyo tilted the balance, gave me the 4th region, and won me the game and the tournament. I may not have been the best athlete or known a gangsta rapper from a gum wrapper, but I got some respect from an unlikely crowd.