In GTA: Vice City, Avery Carrington is a wealthy businessman who hires the player to carry out a few, let's say, underhand tasks to eliminate competitors and bolster his own success. Pretty standard fare for a GTA boss, wouldn't you say? Avery is another character who is, for the most part, entertaining and engaging enough that players won't have been constantly skipping his scenes. He secures himself a place on this list, however, for being the character responsible for forcing players into one of the series' most infuriating missions ever: 'Demolition Man'. The mission involves using a remote control helicopter to drop bombs into various targets of a rival company's construction and levelling the building. This of course takes place while also ensuring the helicopter is not destroyed first by attackers. In principle this sounds like a fun mission and, once completed, players will probably look back on it with a fair fondness. In practice this was far from the case, though, and the fiddly mechanics of the controls coupled with the helicopter's errant propensity for exploding made for a truly frustrating affair. For forcing such agonising annoyance upon us, Avery Carrington makes this list and deserves a place roasting for eternity in pixel hell.