26. Carmen Sandiego
Game: Where in the World is Carmen Sandiego?
What Makes Her Bad: Master thief and master of all disguises. Carmen's always out to get into some mischief.
What Makes Her Cool: That dashing red hat! That darling red coat! Carmen, where do you shop? How come you're so great at teaching us geography?
Carmen Sandiego's certainly a familiar face for those of us who were lucky enough to grow up with the educational software she often starred in, ranging from teaching us math, art, and geography. And though she was a master thief, she always had time to ensure kids learned where South America was and could point it out on a map. Charming, Carmen. We love you.