As a supervillain, the Penguin is one odd duck but for one reason or another he has stuck it out through the years and is arguably Batman's most well known villain second only to the Joker. Oswald Cobblepot AKA the Penguin first appeared in 1941 in the pages of Detective Comics #58. His first on screen appearance belonged to the 1960's Batman series followed by the 1966 theatrical film. No doubt this portrayal, complete with quack laugh, is what earned Pengy such a lasting legacy.
The Penguin was next spotted in animated spin-off of the 1960's series Batman with Robin the Boy Wonder.
During the 70's the Penguin landed a couple of guest spots on Scooby-Doo along with the Joker and teh Dynamic Duo.
In the 1977 New Adventures of Batman series, very little had changed with the Penguin's look since the previous series nearly 10 years prior.
Just in time to support a Super Powers action figure, the Penguin made a single Super Friends appearance during the shows final incarnation, The Super Powers Team: Galactic Guardians. In the episode, Penguin managed to possess, albeit briefly, Superman's powers.
In 1992, the Penguin received the opposite of a face lift when Tim Burton created a grotesque version of the character with webbed fingers and an army of actual penguins for Batman Returns. Oh and he ate raw fish- and not your sushi variety.
The Penguin in Batman: The Animated Series somewhat reflected the new film version of the character in appearance, mostly in stature, but was toned down quite a bit. Penguin was the star of some of the series worst episodes like I've Got Batman in my Basement.
When it was time to redesign characters for The New Batman Adventures, Penguin was once again given a bit more of a dignified look and became more of a mobster than a circus freak.
This incarnation of the Penguin served as one of the main villains in the DTV Batman: Mystery of the Batwoman in which he used his Iceberg Lounge as a legitimate front for his dirty dealings. Though the Penguin would not appear in Justice League, his Lounge was seen on occasion.
The Batman decided to go back to the more outrageous version of the character, though to make him more menacing he was given Wolverine inspired Kabuki henchwomen. Also, the Penguins family of the Cobblepot's was given a long standing rivalry with the Alfred Pennyworth (Bruce Wayne's butler) family. This version was pretty detestable, though like many other versions still pretty lame.
In 2009, the Penguin along with a slew of other classic Batman foes appeared on Batman: The Brave and the Bold. This incarnation payed heavy homage to the 1960's live action incarnation. Penguin would finally get his own main villain story in 2010's Aquaman's Outrageous Adventure in which Batman and Aquaman (along with Mera and Aqualad) were needed to take down the bird. In a series with foes like Kite Man, the Planetmaster, and Babyface, the Penguin finally fits right in.