Portal

There hasn't been a more universally loved and embraced villainess in a long time since GLaDOS in the Portal series. Witty, passive-aggressive, quirky and simultaneously discouraging, GLaDOS was like a private school tutor you didn't have to pay to make you feel dumb. Responsible for testing and maintenance at the Aperture Science research facility, she was also responsible for murdering the whole staff with a deadly neurotoxin. A bloodthirsty AI's work is never done. Often compared to HAL 9000 but with a better sense of comedic timing and signature choppy and endearing text to voice program, GLaDOS, is our favorite computerized killing machine. Plus, what video game character has ever gone on to have a successful post gaming singing career?