"The Driver" Mission in GTA: Vice City (a race between a powerful muscle car vs ya in a slow sentinel; the police chase just make it worst).
Oh god, this. You basically had to luck out that he would end up driving over the spike trap, or flipping off into the water, or something. Hated that mission so much.
Luckily they're mostly optional, but the hostage rescue missions in Red Faction: Guerilla hold a special place deep down in the fiery bowels of my heart:
*Punch a hole through the barricades and guards with your vehicle, then plough into the building holding the hostages. Step out, and try to untie hostages using the same key as "swap weapon with one on the ground". You better bloody well hope there weren't any guards in the room with the hostage, otherwise you can spend about 5 seconds of picking up and dropping weapons before the game realises that yes, you do in fact want to untie the hostage you're aiming the reticule at (all the while you/your ride out are getting shot to all-hell).
Repeat another two or 3 times to free all the hostages, and then begin the arduous task of actually getting them in the get-away vehicle. "Damnit, stop fighting them, and get in. No, don't [censored] get out again, damnit. Oh FFS, STOP STANDING RIGHT BEHIND THE BLOODY REAR WHEELS WHEN I'M TRYING TO REVERSE, YOU GOD-DAMN RETARDS!" All the meanwhile your vehicle is still getting hammered like an alcoholic uncle at an open bar, so by the time the mental defects you're trying to save stop playing hero and actually get in the god-damn car, you're a gentle breeze away from blowing sky-[censored]-high. And of course, to top it all off, each hostage you lose is a huge morale drop, and the longer you're there the more guards spawn.