7. Hitting The Train Ramp - GTA: San Andreas
Oh yes, this one. Wrong Side of the Tracks was one of a handful of missions that showed the game engine Rockstar first conceived for GTA III just wasn't built to handle the grandiose nature of their mission design - let alone giving you any sense of reliability behind the controls. Basically you're supposed to jump a dirtbike onto a moving train - something that would make a return in GTA V when the devs finally had some good weight behind the vehicle itself - but back when the bikes all handled like firecrackers with handlebars attached, trying to aim that in any remotely specific direction was just impossible. https://www.youtube.com/watch?v=cO-0Fu4KsZY To make matters worse there were no checkpoints, and you had the otherwise-likeable Big Smoke chastising your every move if you failed; "Come on CJ", "All you had to do was follow the damn trail CJ!" Agony.