227: Fire Emblem: Radiant Dawn (Wii) on the hardest setting would probably qualify as sadistic to most people. There are hour-long maps that you have to get through without the normal difficulty's in-map save, and every character you use is subject to permadeath if you make a stupid mistake. Great game, especially since you can send annoying characters to their deaths to silence them forever. Good times.
The original Red Faction can be sadistic because of the rail driver. All of a sudden in the middle of the game everyone has the ability to shoot through walls for a one-hit kill, because science apparently created a gun specifically for douchebags.
Jet Force Gemini for the N64 is probably the most sadistic game ever made, though. You're armed with a ton of explosives that make things explode, and levels are littered with these adorable little bear-alien things who you're supposed to save. Shooting them with rockets makes them explode into red goo, though, and it's impossible to not do this. Repeatedly. Problem is, you have to save
every single one in
every single level to actually finish the game. Sure, they come back to life if you restart the level, but you'll just end up shooting them again, laughing maniacally all the while. I'm not even kidding. Anyone who claims to have beaten JFG is a dirty liar.
honestly, it's always kind of baffled me how people could have trouble finding all the tribals when most of them were in plain sight. I think I got most of them first time through the levels, with the obvious exceptions of levels that required the jetpacks.
now, getting the medals for Floyd's levels is pretty ridiculous, getting the earplugs is a more understandable road block to completing the game.
and the mantis twins / mizar 2 were pretty rough.