King Boo (Mario Kart): Hit
My ex-girlfriend: Hit (it asked me a series of questions like "Have you kissed your character on the lips?" and "is your character a female"...then it asked me if she was a long-bearded French journalist from St. Louis
BJ Upton: Miss, guessed Longoria, but at least he didn't guess Joba or Lowrie or something...wait, he guessed Robinson Cano on the 2nd try
Clayface: Miss, guessed Mr. Freeze, and the Schwarzenegger version at that
...then Skeletor, then Apocalypse.