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Penguin

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Real Identity: Oswald Chesterfield Cobblepot
Appearances: Legends of the Dark Mite!, Mayhem of the Music Meister!, Aquaman's Outrageous Adventure!, Sidekicks Assemble! (Simulation), Chill of the Night!, The Last Patrol!, Bat-Mite Presents: Batman's Strangest Cases! (The New Scooby-Doo Movies Universe), Night of the Batmen!, Crisis: 22,300 Miles Above Earth!, and Mitefall!
Skills: Organized Crime, Information Gathering, Martial Arts, Avian Training, and Trick Umbrellas
Voiced By: Stephen Root and Jeff Bennett (Scooby-Doo)

Oswald Cobblepot was born into an upper class family who got wealthy from criminal activity. Cobblept was constantly bullied for being short, fat, and having a beak-like nose. His father died during his childhood from pneumonia after getting soaked in a rainstorm. From that point on, Mrs. Cobblepot made her son carry an umbrella. Soon after, he carried on the Cobblepot tradition and became a criminal. While maintaining a public persona as an entrepreneur and owner of the popular Iceberg Lounge nightclub, Penguin carries out a criminal enterprise such as theft, information brokering, and fencing. Penguin is notorious for keeping and training an army of various birds to carry out his crimes, concealing weapons in his umbrellas, and hiding a pistol in his top hat.

The Penguin became part of Bat Mite's imagined day as Batman. Months later, the Penguin went on a crime spree in Gotham City and escaped from Batman twice. It turned out that he was planning to launch hundreds of umbrella drones all over Gotham and spray civilians with paralytic gas. As a bonus, he caught Batman and tied him to a Drinking Bird death trap. After this scheme succeeded, Penguin vowed he would become king of the Gotham crime world. However, while gloating, he accidentally activated a communication line to Aquaman. The Aquaman Family arrived in Gotham City, deviating from their vacation, and were caught, too. Aquaman used his telepathy to summon crabs near Pier 4 and steal back the utility belt for Batman to escape. With everyone free, Aquaman decalred this caper "Flight of the Penguin." Batman safely detonated the drones in the ocean and chased after the Penguin. With Queen Mera's blessing, Aquaman followed. The final battle took place aboard the Penguin's Submarine where Batman defeated him. He and his henchmen were arrested by the Gotham City Police Department and imprisoned at Blackgate Penitentiary.

The Penguin later appeared at an arms sale conducted by Joe Chill. He and the other villains in attendance fought Batman to no avail and escaped when the roof gave way. He resurfaced and captured Batman and Batgirl. In his moment of triumph, Penguin lowered them into a pit lined with sharpened umbrella tips.

In a parallel universe, the Penguin once teamed up with Joker to try and locate the hidden fortune of the deceased gangster Bennie Bodog Benson. After narrowing the location to a music hall, they concocted a costume and haunted the theater as the Footlight Phantom to scare off the public. On the night of a performance by Weird Al Yankovic, Mystery Incorporated arrived and became entangled in the mystery of the phantom. When they discovered the phantom was the Joker, the Penguin appeared and helped tie up the gang. Batman and Robin later arrived to offer their assistance and stop Joker and Penguin. Bat-Mite was observing this event and gave Batman, Robin, Scooby-Doo, and Shaggy Rogers the ability to fight back and defeat the duo.