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For me most any shooter or fighting game- I love'em but have never been fanatical enough to try to "Finish him!" The most difficult games I enjoyed trying to beat would be:
1. R-Type- dying has seldom been that much fun
2. Gradius- Arrgh!
3. Castelvania- still have the game, still trying
4. Super Contra (SNES version)- i can get to the 3rd level, aftet that...
5. Herzog Zwei (Genesis)- has any ever finished this game?
6. Ghosts and Goblins/Super Ghouls and Ghosts- sometimes I get to the end of the 1st level- sometimes...
7. Punch Out- I'm coming for you Mr. Sandman!
8. Any Civilization game on any level other than default- it's hard to beat a tank with a spearman...
9. Ninja Gaiden (any version)- I like it because it's hard- and can't beat it for the same reason...
10. Eternal Champions (including Sega CD version)- made to the final boss once

On the flip side, the most difficult game I did beat w/o the help of walkthrus, strategy guide, cheat code, etc.- Deadly Towers for the NES. Talk about figuring things out as you go along!