You play as Amanda Ripley in this 2014 title
Alien Isolation
She's a naked blue chick, for important plot reasons
Cortana
A Canadian Punch-Out series character - from what I know of Canada, eerily accurate
Bear Hugger
This AI and Kinect-driven twee lad now only lives on as a Phil impression, pining for his father to remember him
Project Milo
These AI-powered racers supposedly mimic the playstyle of the players they're based on
Drivatars
Master Higgins rides a skateboard in this classic game
Adventure Island
You won't be glad to encounter this AI and the hoops she makes you jump through
GLaDOS
This suggestively-titled game was inspired from Bungie's long-running April Fools' Day gag "Pimps at Sea"
Age of Booty
This is the acronym used to describe an AI-driven character - now sometimes used to insult someone who doesn't think for themselves
NPC
This artificial life video game series features the Norns
Creatures
This NBA player graced many video game covers. Don't ask him about practice, he doesn't care to talk about it.
Allen Iverson
The (if I may editorialize slightly, matter of fact yet oddly alluring) AI companion in Shin Megami Tensei 4 shares a name with William S and Edgar Rice
Burroughs
This man recently received a jail sentence for pirating Nintendo games. Given his name that's ironic - or perhaps oddly fitting
Gary Bowser
This Microsoft shooter helped popularize "behavior trees", an AI technique that shone in its squad vs squad combat
Halo 2
This game, which won 3 awards at the 2006 independent game festival and was an early nu-indie success story, features artificially intelligent polygons under attack from a computer virus
Darwinia
It was the early 2000s, so it was time for this roller blading video game
Aggressive Inline
In the year 3000 the world is at peace. To retain their fighting instinct, humans create this system to simulate historical battles. (Which of course goes horribly wrong)
The Gain Ground system
This character / cryptid is the Canadian representative in the Darkstalkers series
Sasquatch
This 3DS tactics game, published by Nintendo, failed to make waves in part due to long periods of inactivity when the enemy AI planned moves
Code Name S.T.E.A.M.
This IBM chess computer was the first to win a game under normal conditions against a world champion.
Deep Blue
According to IGN's Juan Castro, this 2004 Sega title is "Frankenstein meets Pokemon meets Mario Party"
Amazing Island
The main antagonist of the System Shock games
SHODAN
This video game designer is Canadian and made a pirate-themed game, so he had to be the final question in this category
Sid Meier
This 2005 first-person shooter psychological horror game had famously good AI thanks to it's use of GOAP (Goal Oriented Action Planning)
F.E.A.R.
The name for Nvidia's AI-powered upscaling technology
DLSS aka Deep Learning Super Sampling