I'm playing through Mafia at the moment, a title about 1930's American gangsters that despite it's age still stands the test of time and manages to beat the shit out of many modern games imho.
Anyway, one of the missions involves your character racing and it is so damn hard because you have to go past 5 laps and come first place. I literally spent an hour trying to do it before finally giving up and looking for some walkthroughs/cheats on the web. Funny thing is, upon returning to the mission ready to give up and cheat I decided to try it one last time and I won! The handling on the cars is terrible, unless you slow down on the corners you are dogmeat and if you manage to hit sand or grass your car spins and it's extremely hard to get back into the race again.
I think this is definately one of the hardest missions I've ever had to get through and it is notoriously known to Mafia players to be the mission where everyone gives up and stops playing. Stupid thing is, with the patch you can set the difficulty to easy and the cars always crash so you have plenty of time to get into the lead :roll:
Another one that springs to mind is one of the last missions on GTA3, you have to drive an armoured truck from one island to another with a full wanted level, also there's another one where you must race from Staunton to Shoreside Vale Airport to collect some packages being dropped by a plane at a certain time and by collecting them you get a full wanted level again.. that pissed me off so much.
System Shock 2's 'Body Of The Many' also induced massive headaches several times.
Share your frustrating gaming stories here!