Super Ghouls N' Ghosts.
"FINALLY I BEAT THE GAME!!!! wait... WHAT?! I HAVE TO DO IT AGAIN!?!?!?BLLARRRRRGH"
Super Mario Bros for the NES
-with the whole if you die you have to start ALL over again.
2D Prince of Persia
-also very evil
Super Mario World
-only the super secret levels, and as long as you don't use the cape or yoshi.
Super Mario Bros. 3 Battle Mode
- if you play for a long time with someone else it gets very very hardcore.
And yeah possibly also the Prinny game for psp
- can get very very challenging on hard mode
Flash Meat boy
-as long as you've got a mapped USB controller
and tons and tons of snes and nes games that are hardcore but only because of their horrible game mechanics :P