Shadow Madness on PS1
Everything about the gameplay is just bad, not terrible per-se but it just is so lackluster and unimaginative, it's an obvious rip-off of other RPGs of it's time with it's Active Battle System that pales in comparison to the games it rips off. Your level cap is the most arbitrary thing I've ever seen outside a D&D game... 14... really? The itemization is awful with literally dozens and dozens of useless items that do nothing, and another dozens and dozens of restorative items that heal between 1 and 5 HP.
So why do I love it? It has in my mind one of the absolute best and most interesting stories and settings of any RPG of it's type (meaning console RPGs) The setting is dark and moody and creates a wonderful atmosphere that is very tongue in cheek while combining facets of westerns, steampunk, urban and dark fantasy, and gothic horror. The story writing is top-notch thanks mostly due to it being an actual American company that made the game with more western sensibilities (I love you Japan but you can't give me this level of personally identifiable culture).
So yeah, I still love Shadow Madness as one of my favorite RPGs on the PS1 (and this coming from someone who played the Final Fantasys, the Wild ARMs, the Legend of Dragoon, Suikodens, and Legacy of Legaia.