For me it was Mike Tyson's Punch Out... Glass Joe, he just stand's there... MOCKING ME!!!
But seriuosly, the old days of 8 bit NES, those games/bosses were killer. Just try beating the final boss in Ghosts-n-Goblins, and that's after you reach him and get greated with a screen saying it's all been a dream or something and you have to make the entire journey to him... AGAIN!!!
Also, I remember the final boss in Golgo 13 being quite difficult. As was the Grim Reaper in the original Castlevania, strange when mini-bosses are much harder than the final ones.
And for those complaining about Madden... try playing against a CPU on Tecmo Super Bowl, when the pass is CLEARLY 15 feet over a receiver's head and then suddenly this cutscene starts and you see him leap skyward and come down with the pass, or when your receiver is open by 10 yards but the defensive back suddenly turns on super speed and streaks to him and makes the pick, or even worse when you have 3 DB's literally on top of Jerry Rice so that the sprites aren't even visible and yet he hauls in the pass from Young or Montana... maddening!!!
Oh well, toodles...
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