5. Dildo Dodo
Game: Vice City
Objective- Pilot a seaplane and drop off wave after wave of pornographic flyers around Vice City.
Why is it hard: If you make the slightest mistake whether its a slight scrape against a building or an actual derail, you are SOL. You just will not have enough gas to complete the track. It also doesnt help that the seaplane controls like ass, which is nothing new to airborne gameplay in the franchise. It almost feels like youre required to fly at a specific elevation and speed while flying a perfect run of the fastest possible completion route. In other words, once you do the mission around 20 times you might get lucky enough to complete it.