The game was fun to some degree, just required an unfair time investment. The final fight was a memorably bad experience though. I was like eleven years old when I made it to the end and swear I spent almost a full hour clawing at Scar before I figured out that I wasn’t actually doing damage.
My first thought is The Fortress of Doctor Radiaki for DOS.
A game I never played but is still memorable is early 2000s there was a game in Babbages in my local mall called “Prison Tycoon” that had a cop beating a black man on the box.