The number one spot on this list could be reserved for none other than the manipulative, narcissistic GlaDOS. While she clearly owes a huge debt to HAL and SHODAN for her existence and name alike, she effortlessly overtook her progenitors in pop-culture thanks largely to the efforts of writer Erik Woolpaw: GLaDOS is funny. The relationship between GLaDOS and Portals mute protagonist, Chell, spans two games and is sometimes (not unreasonably) compared to a love story. While shes a constant presence in the test chambers that act as Portals training wheels, GLaDOS only truly speaks to you when you spectacularly fail to die like she wanted for her, the first date and the break-up happen almost simultaneously. From that point on GLaDOS is your jilted ex, and much of the humour in Portal 2 is classic rom-com material -- two people who hate each other being forced to work together, only with more neurotoxin. Its a twist that helps keep the humour fresh until the very end had GLaDOS been merely a threatening AI, thered have been very little room to develop her further. Instead, once stripped of her power and turned into an experiment herself, GLaDOS is able to develop as a character, lick her emotional wounds and eventually convince herself that shes dumping Chell -- not the other way around.While many of the villains on this list exist to be defeated by the players actions, GLaDOS exists to be at least partially redeemed, though thankfully she remains a self-serving, passive-aggressive psychopath. After all, everyone loves a good villain.