Oswald Cobblepot is a psychopathic low level assistance to Gotham Mob Boss Fish Mooney in Gotham City's Underworld. He is portrayed by Robin Lord Taylor, who went to recieve praise for his performace as the soon to be Penguin. He appears as one of the main antagonists throughout the entire series and the archenemy of Jim Gordon, although the pair of them do occasionally put their differences aside to deal with deadlier threats in Gotham.
At some point, Oswald Cobblepot entered the criminal underworld through Fish Mooney and her gang. He received the nickname "Penguin", which he despises.
Oswald Cobblepot was tired of being a lackey of Fish Mooney. He quickly sold her out to Crispus Allen and Renee Montoya of his own free will. Fish soon finds out, and James Gordon is assigned by Carmine Falcone to dispose of the traitor. Gordon tricks Harvey Bullock by pretending to kill Cobblepot, who drops into the river. He resurfaces once the cops are gone, however, and proceeds to murder a fisherman for his sandwich.
Later, he appears once more in the countryside after walking for a while, and he attempts to hitch-hike his way back to Gotham City. He is picked up by two jocks in an SUV, and is grateful for their help. However, they make fun of him and ask him if anyone has ever told him that he walked like a penguin; infuriated, Cobblepot broke a beer bottle and stabbed the man in the passenger seat before taking over the SUV. Hiding the bodies in a garbage bag, Cobblepot drove to a small trailer park and rented a small trailer for $100 a week. He attempts to call the surviving kid's mother to get $10,000 in exchange for his release, but she does not believe him, and he, in turn, confronts the hostage once she hangs up.
Cobblepot returns to Gotham City, and quickly runs into a thug who tries to sell him out to Fish. Cobblepot stabs the man before ordering a tuna sandwhich and pursuing a job. He is soon hired at an Italian restaurant after mysteriously confronting a man who shares his shoe size. While working in the restaurant, he overhears gangster Sal Maroni talking to an associate about their plans to overthrow Falcone. Maroni realizes that Cobblepot was listening and pays him to keep the conversation a secret. Later, Jim Gordon is shocked to discover Cobblepot, dressed in a tuxedo and a grin, at his front door.
Gordon leads Cobblepot to an alley and attacks him, but stops when Cobblepot offers to be Gordon's "secret agent" in the mob. Later, Cobblepot is promoted from diswasher to restaurant manager at Maroni's Italian restaurant because he protected a bag of money when the restaurant was attacked by men who supposedly worked for Falcone. In order to prove that Gordon can trust him, Cobblepot warns him of an upcoming assasination attempt on one of Maroni's foes (Gordon realizes that the target is Gotham City's Mayor). Cobblepot is then revealed to have planned the attack on the restaurant. He visits the men who assisted him and gives them free cannoli, which turns out to be poisoned.