Greetings, Batman! You have taken the bait, as I knew you would. Now, prepare to meet your end, within my Aviary of Doom!
~ The Penguin menacing Batman in "Almost Got 'Im"
Oswald Chesterfield Cobblepot, also known as The Penguin, is one of Batman's primary antagonists within the DC Animated Universe. He was a villainous businessman and crime lord in Gotham City and one of Batman's long-time enemies.
He is a major antagonist in Batman: The Animated Series and its sequel series The New Batman Adventures, a guest antagonist of Superman: The Animated Series and the main antagonist of the 2003 direct-to-video film Batman: Mystery of the Batwoman.
In both Batman: The Animated Series and The New Batman Adventures, as well as in Superman; The Animated Series, he was voiced by Paul Williams. In Batman: Mystery of the Batwoman, he was voiced by the late David Ogden Stiers, who also played Governor Ratcliffe in Disney's Pocahontas.
Oswald Chesterfield Cobblepot was a Gotham kingpin who used his affluent status for the various crimes he committed. He was known as a "gentleman of crime" executing them with class and elegance, along with bird-related themes. The Penguin later nestled himself down at the Iceberg Lounge, a legitimate club, but kept a shady business in the back room. He has had dealings with almost all of Batman's enemies such as Two FaceKiller Croc and Joker
Superman the Animated Series
In the episode "Knight Time" Batman (Superman in disguise) and Robin interrogate him about the whereabouts of the Mad Hatter.
While not appearing his costume appears in the episode "Black Out".
Batman: Mystery of the Batwoman
The Penguin is the main antagonist in Batman: Mystery of the Batwoman. He would ally with Rupert Thorne to smuggle illegal weapons to Kaznia. As Batwoman interfered with one road shipment and his factory went up in a blaze, the Penguin knew that their muscle Carlton Duquesne was out of his league. As the Penguin and Thorne were discussing whom their new muscle would be, Batwoman snuck into the Penguin's file cabinet. The two caught her. But a fight was unleashed and Thorne agreed with the Penguin that they needed to bring someone better in as Batwoman escaped.
While at his lounge, the Penguin called up Bane. Bane agreed to meet him in the Penguin's frequently used back entrance. As soon as the Penguin got off the phone, Batwoman appeared and wrapped a metallic alloy around him. She squeezed and squeezed him until the Penguin gave in and said "Bane" very mildly. It didn't take long for the Penguin's henchwomen and Batwoman to fight. Their fight got taken out into the lounge and the Penguin shot motion-seeking missiles. As Penguin aimed the missile launching umbrella at Batwoman, Batman came in and the Penguin was pushed to the ground. As Batwoman escaped, Batman was pushed into the lounge's center arctic pool. As the Penguin shot homing missiles into the water, Batman set and detonated a bomb from inside the pool. It caused the lounge to flood. The Penguin sat whipped in the face by one of his seals.
The Penguin, Thorne, and Duquesne met with Bane at an isolated warehouse, for Bane could not come to the lounge due to the previous incident. The Penguin allowed him full control of the operation and showed him the ship and plans he was to be using. Later that night, as the Penguin and Thorne played cards, they got a call to come to the ship. To their surprise, Bane found out who Batwoman was; Kathy Duquesne, Carlton Duquesne's daughter. Batman soon came in and another fight was unleashed. After Batman and Kathy escaped, the Penguin and Thorne ran to Penguin's boat to retreat for the bomb Kathy had was missing. They ran into the other two Batwoman. As the ship exploded, Sonia was injured and Rocky went after the fleeing felons. She latched onto the boat and the sudden stop made the Penguin and Thorne fly into the water. They were caught, and the Penguin, after years of being "reformed," was finally punished for his crimes and sent back to Stonegate with Thorne.
Justice League Unlimited
In the episode "This Little Piggy" his famous club the Iceberg Lounge is shown. It is later mentioned that he kidnapped a celebrity and Batman had to go undercover for about a month to catch him.