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The Penguin later attended the Joker's 'Superhero Celebrity Roast', where the Joker was roasting Batman alive. He was eventually caught and apprehended. The Penguin attempted to escape in his submarine, which he revealed to also be a land vehicle. The Penguin later held up the wealthy passengers on a yacht, but was intercepted by Aquaman, who was disguised as Batman. Bat-Mite was observing this event and gave Batman, Robin, Scooby-Doo, and Shaggy Rogers the ability to fight back and defeat the duo. Batman and Robin later arrived to offer their assistance and stop the Joker and the Penguin. When they discovered the phantom was the Joker, the Penguin appeared and helped tie up the gang. On the night of a performance by Weird Al Yankovic, Mystery Incorporated arrived and became entangled in the mystery of the phantom.
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After narrowing the location to a music hall, they concocted a costume and haunted the theater as the Foot light Phantom to scare off the public. In a parallel universe, the Penguin once teamed up with the Joker to try and locate the hidden fortune of the deceased gangster named Bennie Bodog Benson. In his moment of triumph, the Penguin lowered them into a pit lined with sharpened umbrella/parasol tips. He resurfaced and captured Batman and Batgirl. He and the other villains in attendance fought Batman to no avail and escaped when the roof gave way. The Penguin later appeared at an arms sale conducted by Joe Chill. He and his henchmen were arrested by the Gotham City Police Department and imprisoned at Blackgate Penitentiary. The final battle took place aboard the Penguin's submarine where Batman defeated him. With Queen Mera's blessing, Aquaman followed. With everyone free, Aquaman declared this caper "Flight of the Penguin." Batman safely detonated the drones in the ocean and chased after the Penguin. Aquaman used his telepathy to summon crabs near Pier 4 and steal back the utility belt for Batman to escape. The Aquaman Family arrived in Gotham City, deviating from their vacation, and were caught, too. However, while gloating, he accidentally activated a communication line to Aquaman.
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After this scheme succeeded, Penguin vowed he would become king of the Gotham crime world. As a bonus, he caught Batman and tied him to a Drinking Bird death trap. It turned out that he was planning to launch hundreds of umbrella/parasol drones all over Gotham and spray civilians with paralytic gas. Months later, the Penguin went on a crime spree in Gotham City and escaped from Batman twice. The Penguin became part of Bat Mite's imagined day as Batman. He commits crimes to lead Batman and Robin to his antics. Penguin is notorious for keeping and training an army of various birds to carry out his crimes, concealing weapons in his umbrellas/parasols, and hiding a pistol in his top hat. While maintaining a public persona as an entrepreneur and owner of the popular Iceberg Lounge nightclub, the Penguin carries out a criminal enterprise such as theft, information brokering, and fencing. Soon after, he carried on the Cobblepot tradition and became a criminal/terrorist. Cobblepot made a point to have her son carry an umbrella at all times. His father died during his childhood from pneumonia after getting soaked in a rainstorm. Cobblepot was constantly bullied for being short, fat, and having a beak-like nose. The Penguin aka Oswald Chesterfield Cobblepot was born into an upper class family who got wealthy from criminal activity.