2. Supply Lines...
Game: San Andreas
Objective: Zero wants you to take out his Nemesis courier business using an RC helicopter. The result is arguably the hardest mission of the franchise, something so broken future versions of the game had a modified version that was STILL stupidly hard. If this mission were actually required to complete the game a good amount of players including myself would have never finished.
Why is it hard: Like everything else capable of going airborne in Grand Theft Auto the RC helicopter controls like garbage. Similar to a previous selection (Dildo Dodo) it requires a ludicrous amount of luck with time management and fuel. Only this time your enemies occasionally fight back and you have very limited health. The mission is so absurdly difficult it isnt even worth attempting unless you are a completionist.