Pilotwings (SNES)

How I would sum this game up:  Skydiving for lazy people.

I owned this game as a kid and hated it.  Upon replay, it is very fun and addictive.  The difference is years of thumb training and patience.  You can parachute, fly, jet pack...  everything you are too scared to even consider in reality.  They all require a little bit different technique, but they are all fun.

To enhance the realism of the flying levels, get drunk (I GOT YOU, commercial pilots!  In your FACE!)