One of the Most Perfect Frame-Ups (DETECTIVE COMICS #58, 1941)
The Penguin first appeared in 1941's DETECTIVE COMICS #58 as a short and stubby, pointy-nosed man dressed to the nines and carrying an umbrella. Stealing a priceless painting right under Batman’s nose, this classy criminal went on to become the ringleader of a string of robberies and in a genius move, framed Batman for theft during one of those attempts. Although Batman was later exonerated and prevented the Penguin from further executing his plan, the “gentleman of crime” was able to escape and cemented his status as a worthy adversary of Batman.
Knights of Knavery (BATMAN #25, 1944)
When the Penguin was captured and tossed into prison once more, in 1944's BATMAN #25, he found himself in the company of his new cellmate—the Joker. As the two arch-criminals bantered back and forth as to who would rule Gotham’s underworld, they eventually struck a wager: whoever steals the Van Landorpf Emerald claims his right to remain in Gotham City. After breaking out of prison, they both set off to make plans of stealing the Emerald. When Batman caught wind of their escape, he and Robin set a trap for them and their gangs. To avoid capture, Penguin and the Joker teamed up, a first for these two iconic villains, to take on Batman and Robin. Although they had to abort mission of stealing the Emerald, they discovered a newfound respect for each other’s talents and formed a full partnership. Gotham was no match for this dastardly duo as crime and corruption swept the city. During another attempt to apprehend the Penguin and the Joker, Batman and Robin were captured instead and taken to their shared hideout. When they couldn’t agree on how to kill the Dynamic Duo, Batman took advantage by pitting them against one another. Their puffed up egos and stubbornness contributed to their own demise as Batman and Robin freed themselves and beat their longtime foes into submission.
The Return of the Penguin (BATMAN #155, 1963)
During the Silver Age, the Penguin returned in 1963's BATMAN #155 to renew his battle of wits with Batman. After serving time in jail, the Penguin was released but did not receive the homecoming he expected. Hoodlums began goading him, calling him a has-been and to prove it otherwise. Determined to shake their taunts, the Penguin initiated a new wave of bird-inspired crime in Gotham City. These activities attracted the attention of Batman and Robin who both quickly got on his tail. Picking up on his fowl-patterned deeds, Batman and Robin were steps ahead of the Penguin’s next bird-crime and were able to stop him before he stole pieces from a museum.
"The Origin of the Penguin!" (THE BEST OF DC #10, 1981)
Nearly 40 years after his debut, the Penguin finally got an origin that introduced his overbearing mother, as stated in 1981's THE BEST OF DC #10. As a young boy, Oswald lived in the family bird shop with his mother who had fallen gravely ill. She insisted that her son carry an umbrella at all times, the direct result of her husband being caught in a thunderstorm and dying from bronchial pneumonia 2 weeks later. With an odd name and an even odder body shape, the umbrella was the perfect accessory to garner even more insults. Nonetheless, Oswald attended college and majored in ornithology to complement his love of birds. When Mrs. Cobblepot passed away, Oswald inherited her mountain of debt. To make matters worse, creditors seized the shop and birds living inside. About ready to crack, Oswald turned toward a life of crime, seeking revenge for his tragic youth.
"Emperor Penguin" (DETECTIVE COMICS #13-18, 2012-2013)
In the New 52 storyline “Emperor Penguin”, Oswald Cobblepot was a crime lord in Gotham City and owner of the Iceberg Casino, a place of pleasure and dirty business. Tired of the citizens thinking he was scum, he decided it was time to leave a more permanent mark. It was time that they loved him. With money and of course, force, Oswald persuaded the director of the Neville Community Center to change the new wing from Wayne to Cobblepot. When it was announced, he received praise all around. The cherry on top was him stopping a hit on Bruce Wayne. His plan seemed to go swimmingly until he was called away to help a friend in Arkham. In his absence, his right-hand man Ogilvy was to temporarily oversee his operations. But Ogilvy had an agenda of his own. Calling himself Emperor Penguin, he took control of Penguin’s casino, gang and assets. Rocked by betrayal when he returned, Penguin tried to attack Ogilvy’s new empire, but Batman prevented that plan and the police took him into custody.
This rogue’s reboot included teaming up with a few other lords of organized crime. Together, Penguin, Black Mask and Great White Shark formed an unholy trinity known as “The Black & Whites”. With a common goal, they met with KGBeast, one of the best assassins, and hired him to kill Batman. He agreed so long as they cleaned up the mess he would leave in his wake. As the mayhem began, Great White Shark was concerned about what KGBeast would do to them if he knew they couldn’t pay what they promised him. Penguin told him to leave those worries to him.
Aboard the Silver Dollar Casino boat, KGBeast was holding Batman and Harvey Dent captive. The Black & Whites were also present and Penguin demanded that Harvey give them the access code to his blackmail files. Suddenly there was an explosion, and Batman and Harvey Dent got away. The casino boat, no longer anchored, started to drift toward the river falls. But Batman stopped the boat from going over and the trio went underground.