Last Battle - a Genesis beat em up with no continues, 1 life, but man when your shirt rips off and you punch at lightning speed, its really cool
Megaman X7 - I try to deny it's terribleness for a small time to try to beat it.... still no avail.
(retired) Dark Souls 1+2, I loved Demon's souls, but man Dark souls' difficulty isn't hard, it's cheap, the broken hit-boxes speak for themselves. still fun to play at times.
Sonic 3D Blast (Genesis) - This game really isn't too horrible, it's soundtrack alone was so good that tracks were re-used in sonic adventure. which is the main reason I play it time to time.
X-Kaliber 2097 - Pretty medicre platformer with broken bossfights, but dat setting and dat music, it's my most guilty pleasure