8. Shadow Man (PS1)
The saddest thing about Shadow Mans inclusion on this list is that I spent more hours of my childhood exploring the twisted realm of Deadside, than I did any other video game world. But lets be honest here: Shadow Man was a very ugly game, and in some instances practically unplayable. When Shadow Man was released in 1999 it explored some heavy themes (evil voodoo, torture, serial murder, etc) and the way it explored these was particularly noteworthy. It threw the player head first into an unimaginable world of misery and pain, and forced the player to endure that misery in order to progress literally, the only relatively safe areas of the game, Liveside, render Shadow Man powerless. However, if you were unfortunate enough to own the Play Station version then your experience would have been utterly ruined by shoddy animation, bizarre graphical glitches, poor frame rate and textures that look like they had been done by a contractor off Rouge Traders. The core game had enough questionable design choices as it was: especially its bizarre problem of having fantastic 3D models and environments, but exceptionally dire detailing and textures. Put short, the port should have been locked away in a room down in the darkest depths of the asylum.