15 Most Infuriating Video Game Boss Battles Of The 2000s

5. The Driver - Grand Theft Auto: Vice City

From the copycat to the top dog, GTA's first sequel is one of the greatest in its history, but the mission entitled The Driver - in which you must race a socially-awkward nerd named Hilary around Miami to recruit him - is the nearest thing to an infuriating 'boss fight' GTA has ever had. I simply had to include this godawful bit of mission design as it's all too easy to forget just how plain bad a lot of GTA's older missions truly were. The game engine was never built for anything fancier than physics-based driving and the occasional street race, but by putting the focus on nailing very tight turns and accelerating in just the right spots (all while Hilary darted off ahead, being his AI was bolted to the road), was incredibly off-putting. If you managed to get ahead of him on a turn his AI would simply ram you off the road, and that's if you even got far enough in the race to do so, being GTA's older geometry had a knack for getting you snagged on an outcrop of land, a renegade plant pot or arching off a civilian into the sea. https://www.youtube.com/watch?v=2m5bNydjWOk Failure meant a full restart, and you had to beat this guy to progress in the main story. It's a wonder we ever got to the end, as this sort of thing would get ripped apart if it released nowadays.