- Not to be confused with Fish Mooney's umbrella
- "No one ever respected you. We always saw you for what you really are. A tiny freak who used to hold an umbrella. Nothing more."
- —Gabe to Oswald Cobblepot[src]
Umbrellas are the best known identification signs of Oswald Cobblepot besides penguins. They became associated with the Penguin because of him being the umbrella boy of Fish Mooney before becoming the ruler of Gotham City's criminal underworld. Even when he surpassed being Mooney's lackey, he still had an umbrella as his badge, used as the logo for his nightclubs Oswald's and Iceberg Lounge. Before he got a proper cane, he not only used umbrellas to protect him from rain, but also as a walking aid.
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After Carmine Falcone tested muffins that Liza had prepared for him, he walked outside of his Manor into the rain to crumble and feed them to his chickens. However, Penguin then arrived at Falcone's chicken coop, holding his umbrella over both of them. Don Falcone said Oswald's arrival was apt, as he was just thinking about the day they first met. He marveled that everything had worked out exactly as Penguin predicted; Gordon spared his life, he was now securely placed in Sal Maroni's organization, and even provided a perfect way of getting rid of Nikolai. However, Carmine said he still has doubts about letting Gordon live; he only did so because Cobblepot requested it. Thereupon, Penguin thanked him for sparing Gordon, assuring Falcone that, sooner or later, Gordon will be on their side.
- "My last one got stuck in your throat, so I'm thinking about shoving this one somewhere else."
- —Oswald Cobblepot to Azrael[src]
After Oswald lost his first umbrella, he got a new one that only differed from the predecessor in its handle, an entirely black one.
As soon as he learned about Theo Galavan's revival as Azrael, Penguin immediately returned to Gotham City to kill him once again. He payed Butch Gilzean a visit and convinced him, that not only both of them, but also Gilzean's beloved Tabitha suffered because of Theo, so he has to die. At night, Oswald and Butch tracked down Azrael at Wayne Manor where he was already at battle with James Gordon, Bruce Wayne and Alfred Pennyworth. When Gordon tried to shoot Azrael, Penguin turned up unexpected, ironically telling Jim that he should know by now that bullets don't kill this monster. He then devoted to Theo, explaining him that since his last umbrella got stuck in his throat, so he thinks about shoving this one somewhere else. He then advised James to always bring the right tools for the job before saying 'See you in hell, Theo' to Azrael. Cobblepot tafterwards stepped aside only for Butch to blow up Galavan with a bazooka, killing him once and for all.
- In the DC Comics, Oswald Cobblepot nearly always carried a normal looking umbrella with him, that however had built-in weaponry such as guns, blades, flame-throwers, acid spraying devices or poison darts. He also had some used for modes of transportation such as ones that had a series of built in spinning blades to use as a mini helecopter or a jet powered engine to ride it as a broomstick. These trick umbrellas first appeared in Detective Comics #58.