10 Villains Who Outsmarted Batman

10. Riddler - Batman (Vol. 3) #32

At the closing of the beloved and despised War of Jokes and Riddles storyline, the Riddler manages to outsmart Batman in a very, very unusual way.

After telling Batman that all the terrible things he's done have been more to rile the Joker than to counter Batman, Edward also tells the hero that he could kill everyone he's ever loved easily. In a final, very inadvisable move, Nygma decides to tell the Bat that the only reason he hasn't murdered his family yet is because he keeps Batman around as entertainment, and so he doesn't want to break him.

Naturally, all this makes the Dark Knight more than a little angry. So angry, in fact, that he goes to kill the Riddler with a well placed knife to the face, which is only stopped by the surprising assistance of none other than the Clown Prince of Crime.

While the Joker technically gets to outsmart the Dark Knight because he's the one who stops him breaking his own rules and killing, the Riddler is the one who should get the credit for this Bat breakdown. After all, he's the one who manages to push Batman's buttons so expertly that the hero legitimately gives up all his moral codes in order to get the temporary relief of stabbing the villain clean in the face.