Okay, correct guesses so far:
Keen, Just A Police Man, Generic Star Trek Character, Croft, Croft, Chaplin, McDonald,
Cate Archer, Vader, Stormtrooper, Fett, (No one has gotten this one right yet, look directly below him for a hint), Homer,
Wilco, Guybrush (that is a banana, Guybrush with a gun would be silly, he's probably trying to lure a three-headed monkey somewhere), Fire Mario, Link, Beast, Legoman,
Snow White, Robin Hood, Rincewind, The Luggage, (generic wizard works, but there was a specific one who wasn't Gandalf that I had in mind), Huntchback, Esmerelda
Leeloo (5th element), (nobody's gotten this one yet, she's from a TV show), Purple Tentacle, Green Tentacle, Jessica Rabbit, Marvin, Yoda, (nobody's gotten this one yet, I see the confusion with Chewbacca though, especially right next to Yoda)
I believe I shall do some animating of these in the future. Anyone got any comments/crits for the other two images?