- Not to be confused with Oswald Cobblepot's umbrellas
- "You know, if I close my eyes I can still see you holding Fish's umbrella. Yes, Miss Mooney. No, Miss Mooney. Whatever you say, Miss Mooney. That wig looks great on you, Miss Mooney."
- —Harvey Bullock to Oswald Cobblepot[src]
An ordinary umbrella was owned by Fish Mooney at the time she run her own nightclub in Gotham City. Gaining wealth through her criminal activities as part of the Falcone crime family, Fish eventually employed so-called umbrella boys to carry her umbrella.
Since being the umbrella boy of Fish Mooney allowed Oswald to enter the criminal underworld of Gotham City and gave him his nickname "Penguin", the umbrella became his emblem used as the logo of his nightclubs Oswald's and Iceberg Lounge. He also carried an umbrella with him as a walking aid before owning a proper cane and had umbrellas stitched on his shirtsleeves.
However, even after becoming the king of Gotham, Cobblepot still not managed to lose his still lasting status as umbrella boy. Months after his victory over Fish, Falcone and Maroni, Penguin received a visit by Harvey Bullock who confronted him about the rumors about Jim Gordon collecting a debt for him, but Oswald denied it. During the conversation, Harvey twice told the self proclaimed "King of Gotham" that he still sees him as just an umbrella boy and afterwards warns him not to come after Jim or he'll come after him and still wants revenge for Fish's death. As soon as Bullock left, Oswald angrily broke his cup, but quickly calmed down and asked Gabe for another drink.
After Fish was revived by Hugo Strange and then hunted down by the Penguin, it eventually came to a confrontation between Mooney and Oswald in a forest. When Cobblepot asked her why she did not kill him during their last meeting under a bridge, Mooney told him that she still sees him as her property, calling him "umbrella boy" and explaining that she feels pride for causing him to turn into the Penguin, something she could not destroy. Touched by her speech, Penguin abandoned his plan to shoot his former crime boss and allowed her and Strange to escape after ordering her to leave Gotham for good.
- 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.