5. Captain Skyhawk
This game was listed under the too hard to play, but somehow still awesome file. I owned this game for over a decade, even after I had moved on the next system I still kept my Genesis around to play this game poorly. Seriously, if you watched me play this you would be forced to encourage me to find something else to do, anything else than embarrassing myself with this game. I cant even say with certainty that I got past the third level, it was really hard, but so awesome. Captain Skyhawk was a top down ¾ view jet fighter game where the player piloted an F-14 Tomcat into friggin space! A few games came along after, including a Star Wars PC game and a few stages in the Lego Star Wars series that paid homage to the old format.
Update: Again, a game this simple could be easily updated and improved as a XBLA or PSN game. Different types of jets, two player co-op, and larger 3D environments for starters. The Lego Star Wars flight stages were among my favorite, even then I thought it would be cool to play a complete game with this kind of classic set up. As a bonus I always thought that Robotech could use this format to make a jet/mech game from this perspective.