One of the lamest "Supervillains" happens to be one of Batman's best known - The Penguin. This tuxedo and umbrella loving goon has been in the live action Batman TV series, Batman Returns the movie, Batman: The Animated Series, and The Batman animated show. He even appeared in a crossover of Scooby Doo. If he ever appears again, I just hope he doesn't utter his trademark "quack."
Born Oswald Chesterfield Cobblepot, the Penguin is bullied as a child for his short stature, obesity, and beak-like nose. These traits make him an outcast in his rich, high society family; their rejection drives him to become a criminal. In keeping with his family's tradition of wealth, the Penguin lives a life of crime, yet executes it with his own self-proclaimed class and style.
Unlike most of the Batman villains, the Penguin is a gentleman villain, in control of his own actions and perfectly sane, features that serve to maintain a unique relationship with his archenemy, Batman. This has extended into the current situation with the Penguin ceasing his direct involvement in crime, instead running a nightclub that is popular with the underworld. As such, he is an excellent source of information on crime, so Batman grudgingly tolerates his operations. However, the entrepreneurial Penguin is often fencing stolen property or arranging early furloughs for incarcerated former criminal associates - for a hefty fee, of course - on the side. During the storyline "No Man's Land", when Gotham City is nearly leveled by an earthquake, he stays behind when the US government shuts down and blockades the city. He becomes one of the major players in the mostly-abandoned and lawless city, using his connections to profit. One of these connections is discovered to be Lex Luthor and his company.
The Dark Knight returns in 90 days!