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Real Identity: Oswald Chesterfield Cobblepot
Appearances (BTAS): I've Got Batman in my Basement, The Strange Secret of Bruce Wayne, Dreams in Darkness, Almost Got 'Im, The Mechanic, Birds of a Feather, Blind as a Bat, Second Chance, Batgirl Returns, Joker's Millions, The Ultimate Thrill, Girls' Nite Out, Judgement Day and Mystery of the Batwoman
Appearances (STAS): Knight Time
Appearances (BTAC Comics): The Darker Knight, Red Son Rising Part 2, Red Son Rising Part 3, and Secret Santa
Skills: Business, Underworld Activity and Umbrella Weaponry
Voiced By: Paul Williams/ David Ogden Stiers

Oswald Chesterfield Cobblepot is a dwarfed gangster in Gotham City. Because of his short stature and bizarre appearance (matched with formal clothing), he soon took on the name of the Penguin. The Penguin often commited crimes based on the motif of birds. He stole items based on birds such as priceless antiques, art or weapons and hires henchmen whose names are associated with that of birds.

While his henchmen stole Von Ulster's fabled Faberge Egg, the Penguin sent his specially trained South American vulture, Scrap to intercept Batman. The vulture was followed by two inquisitive children, Sherman Grant and his friend Roberta, to a condemned bird seed plant. Batman arrived and saved the children. He was doused with a toxin sprayed via Penguin's trick umbrella. The Penguin tracked the children to the Grant household, in the suburbs of Gotham. The children managed to stall the Penguin long enough to allow Batman to recover with an anti-toxin. Penguin was arrested and Scrap was donated to the Gotham Zoo.

Though a social outcast, Penguin still desired acceptance. He became an unwitting patsy for Veronica Vreeland as part of a joke at one of her upcoming parties. Penguin took his relationship with Vreeland seriously and went on a series of dates. Despite displaying some odd habits, Penguin saved Veronica from two muggers. He came to close to proposing marriage to Vreeland until her overheard her friend Pierce gloating. Vreeland was kidnapped and held for ransom. After Batman saved her, she admitted to becoming fond of Penguin, as he was hauled away to jail.

After his henchmen narrowly escaped Batman in a high speed chase, Penguin became privy to Batman's secret relationship with ex-Global Motors engineer, Earl Cooper. The Penguin infiltrated Cooper's compund and held his daughter hostage for collateral. He then forced Cooper to rebuild the Batmobile with death traps. However, Cooper snuck in a fail safe to save Batman and Robin.

When Wayne Tech was showing off its stealthy fighter plane, the Raven XII to the military, the Penguin made an appearance. The Raven's stealth mode allowed for recon, cloaking and cutting edge radar thanks to its Zero Visibility Flight (ZVF) system. Penguin hijacked it and ransomed all of Gotham City for $100 million. In the daring theft, Bruce Wayne's retinas were flash burned. Wayne was temporarily blind. Despite recommendations from Dr. Thompkins, Wayne donned the Batman suit to confront the Penguin with a virtual reality aid, adapted from the ZVF. When Jason Todd went solo as Robin, he once kicked Penguin out of a moving helicopter. After emergency surgery on his face, Penguin recovered at his tropical retreat, Key Nest.

Frustrated with constant defeat at the hands of Batman, Penguin devised a more indirect approach at crime. Penguin displayed himself as a reformed individual and became the proprietor of the Iceberg Lounge, Gotham's newest and hottest night club. Behind closed doors, Penguin continued his underworld dealings. He was involved in smuggling, fencing and information rackets. Penguin trafficked stolen goods from the likes of Roxy Rocket, Killer Croc and Two-Face. He also kept himself informed of movement in the underworld such as Livewire's escape while being transferred to GothCorp Labs. At Batgirl and Supergirl's request, Penguin revealed the location of Harley Quinn and Poison Ivy's hideout.

Mr. Freeze hired Penguin to procure the Shawl of Magdalene for him. Some time later, Batman and Azrael went to the Iceberg Lounge to question the Penguin about the Shawl. Penguin lauded them for being civilized and not delivering so much as a concussion to his staff. He offered them a little Arsenic. Batman cut to the point and demanded the Shawl. Penguin revealed he was just the middleman in the transaction and passed it on to the new and anonymous owner. Azrael knocked Penguin's drink and hat off and demanded a name. Penguin called out to Mr. Wing. A giant white humanoid bird entered the office and grabbed Batman. Penguin introduced him as his new wingman and the last name either of them would hear. Mr. Wing couldn't believe he got to ice Batman and some other loser on his first week of work. He told Penguin he had a bonus coming. Penguin ordered him to just finish them off. Batman gave the code "Sword of Salvation" and in unison, he and Azrael kicked Mr. Wing in the gut. He dropped them. Batman teased Azrael he had to skip evening prayers now and then to learn that move.

Azrael chased after Penguin to the balcony then beat the name of the client out of him. He told Azrael it was Mr. Freeze and he was hiding out at Iceland. Batman ran to the balcony and saw Azrael already beat Penguin to a pulp. He deemed Penguin would be Catwoman's substitute and take on her suffering. Penguin was tossed off. Batman snagged one his legs with a rope and pulled him up. Azrael left in the meantime. Penguin recovered in intensive care. The Joker met with Penguin in his office at the Iceberg Lounge. Joker wanted to borrow a couple hundred thousand dollars to go out on the circuit with his goon Straightman. Penguin was suspicious and asked where Harley Quinn was. Joker revealed they were seeing other people but mused she could have said so without a mallet to his forehead. He recalled she was with Poison Ivy last he heard. Penguin wasn't buying his act and knew someone was after him. He preferred to see how it played out. Joker summoned Straightman to explain the situation better. Mr. Wing burst into the office and fought Straightman.

The fight spilled outside and Wing was knocked out. Joker declared he and Straightman were a classic comedy duo. Red Hood retorted except as always, he was the only one laughing then darted Joker and Straightman repeatedly. He declared he was breaking up the act. With a running start, Red Hood delivered a jump kick that propelled Straightman onto the top of the iceberg in the center of the lounge. He then threw a grenade that dislodged the big chandelier. It crashed on top of Straightman. Red Hood collected Joker and told Penguin to tell Batman he came. Some time later, police arrived. Penguin remarked Batman had an uncanny knack for showing up when he either was not wanted or no longer needed. Batman inquired about Straightman while Batgirl looked around with her flashlight. Penguin was irate about his three million dollar chandelier and vowed to hang Red Hood in its place. Batman noted Red Hood didn't say where he was taking the Joker. Penguin was annoyed and answered he wasn't looking to prolong the visit. Batgirl noticed wet streaks and alerted Batman. She recalled the last time it rained in the city was last week. Penguin recalled he got a clammy smell off Red Hood but dismissed it as bad hygiene. Batman realized Red Hood was using the sewer system to hide the whole time and took over Killer Croc's old lair.

The Penguin took a flight out to his tropical retreat Key Nest for the Christmas holiday and hired the Carpenter to repair the Iceberg Lounge in the meantime. He brought Mr. Wing along with him. Wing found it very swank. Penguin recalled he used it after an encounter with the second Robin. Wing looked on the bright side and pointed out the "upgrades" were awesome. Penguin mused he was right then decided to call up the Carpenter and check on her progress with renovations at Iceberg Lounge. He began to suspect there was a party going on. Carpenter lied she had the jukebox playing and hammered a wreath to a pillar. Penguin realized he the Lounge didn't have one. She wished him Merry Christmas and hung up. Later in the party, Batman, disguised as inept henchman Knute Brody, mentioned he saw the police pulling up about ten minutes ago. Carpenter happened to be on the phone with the Penguin again. She told him it wasn't a raid, just Batman singing Christmas carols with the police.

Penguin's largest known smuggling contract involved secret weapons plants used to manufacture and smuggle arms to the East European country, Kasnia. Funded through an alliance with other gang leaders, Rupert Thorne and Carlton Duquesne, Penguin hid the plants behind fronts such as Beak's Bric-a-Brac, a figurine warehouse. Half a billion dollars was paid upfront for weapons such as plasma rifles, laser guns and missile launchers. As lucrative as the deal was, the three incurred the wrath of Batwoman. To make matters worse, Batman and Robin began to investigate. Penguin hired Bane and ceded control to him. The remaining arms were stocked on a luxury cruise liner, S.S. Naiad. Bane ambushed Batwoman, but the remaining Batwomen, Batman and Robin intervened.