51. Penguin

A "gentleman of crime," The Penguin is one of the few Batman villains that is actually in complete control of his actions - he's mostly sane, but we think he'd still do better on some meds.

Oswald Chesterfield Cobblepot was born into a wealthy family and tormented throughout his childhood due to his freakish appearance - his paunchy belly, short stature, and elongated nose earned him the Penguin nickname. And his overbearing widowed mother forced him to always carry an umbrella - convinced he would die of pneumonia like his father were he caught in an unexpected downpour.

Cobblepot's oddball nature caused him to be rejected by his upper-crust family, an experience which turned him to a life of crime -- one that suits him just fine. A master strategist, Penguin uses his considerable intellect, wit, and wealth to manipulate every situation to his advantage. And he executes it with a hoity toity style all his own.

The Penguin is not universally appreciated by Bat-fans, but his place in the pantheon of great comic villains is secured by pop cultural impact alone.