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The world thinks I am dead, the richest spoils in Gotham await me, and you want to cut yourself a slice of the action? -- You must learn, my ghoulish friend, the Penguin flies ever alone!!
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~ The Penguin.
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I have never received the recognition my criminal genius deserves. The Joker and the others-- they're all second rate charlatans compared to me... and yet, because my appearance strikes some as comical-- I have always been portrayed in the media as an insignificant bumbler constantly thwarted by the Batman. But I ask you-- Have any of the others ever fared any better against the Batman? And consider this-- In virtually every confrontation, I have successfully completed at least two or three brilliant crimes before Batman's single victory.
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~ The Penguin.
The Penguin is one of the major antagonists of DC Comics, most notably appearing as one of Batman's oldest and infamous foes.
The Penguin relies heavily on gadgets, since he doesn't have any superpowers. His real name is Oswald Chesterfield Cobblepot. He feels the need to prove himself, because of his somewhat eccentric appearance. Although the Penguin doesn't seem to have any real powers, he appears to be somewhat of a knowledgeable scientist, as his umbrella doubles as a small helicopter device that he uses to fly the skies of Gotham and a pistol concealed in his umbrella. He also uses his umbrella to take down Batman. He owns a nightclub called the Iceberg Lounge which often provides cover for criminals, which Batman can actually tolerate provided he gets information on the criminal underworld. Unlike most of Batman's foes, he is not insane.
The Penguin doesn't appear in the video game Batman: Arkham Asylum, but two of the Riddler's riddles revolves around him. He does have an entry in the character bios. His profile states:
The Penguin, one of Batman`s oldest foes, is an eccentric criminal mastermind, known as much for his love of ornithology and trick umbrellas as for his shady business dealings. Gotham's popular Iceberg Lounge serves as Cobblepot's front for a number of illegal financial activities that fund much of the city's underworld. Despite his short stature, the Penguin is a wily foe whose umbrellas conceal a variety of deadly weapons and gadgets.
Batman: Arkham City
The Penguin is a major antagonist in Batman: Arkham City. At the beginning of the game, The Penguin was waiting for Bruce Wayne, to teach him a lesson for ruining his career. After Wayne managed to escape from Penguin after beating his men and breaking his arm, Penguin did quite a handful of activities.
He managed to capture Mr. Freeze, kidnap Comissioner Gordon's special force, managed to find Solomon Grundy, and somehow aquire TITAN. In the middle of the game, Batman had to find Mr. Freeze, because the Joker poisoned Batman with his own blood.
But the Penguin captured Freeze and held him in the museum, so Batman had to rescue Freeze. Penguin also was using Freeze's freeze gun. After Freeze was rescued, Batman created a device that could jam Freeze's weapons. He uses on the freeze gun which left Penguin vunerable. To prevent himself from being defeated by Batman, Penguin tossed Batman into the hands of Solomon Grundy. After Grundy was defeated, Penguin tried to defeat Batman with a Rocket Launcher, but ended up being defeated by Batman. In the video game, Penguin's personality is different. He's less sophisticated and more bloodthirsty.
Injustice Gods Among Us
Penguin makes a cameo in a Star Labs Mission where he shoot the fighter closest to him.
Oswald Cobblepot appears in the Telltale video game series for Batman. This version is tall, thin and handsome (unlike his comic book counterpart) and is the same age as Bruce Wayne, with the pair of them being childhood friends.
A younger version of Penguin appears in the television series Gotham, where he appears as one of the series' antagonists. He is played by Robin Lord Taylor.
MAD
The Penguin has made appearances in the Cartoon Network show MAD. He gave a safety PSA in episode 11, was shopping in a villain warehouse in episode 20, and was seen at a restaurant in episode 32.
Batman Returns
In the movie Batman Returns, Penguin leads a gang of mischeivous criminals and circus performers called the Circus Gang and tried to take over Gotham City by officially becoming the town's new mayor.
Batman: Assault on Arkham
Penguin appears in Batman: Assault on Arkham, voiced again by Nolan North. He is hired by Amanda Waller to give the Suicide Squad arms, equipment, and shelter in his Iceberg Lounge for the night prior to their mission to infiltrate Arkham Asylum and take out the Riddler. He appears to have worked with Deadshot before and respects him as the city's best assassin, as he chooses to only work with the best, and he holds a grudge against the Joker and Harley Quinn for their having sunk a truck of his cigarettes "just for a laugh."
Batman: Bad Blood
The Penguin briefly appears at the end of the film Batman: Bad Blood in a non-speaking role. Penguin is seen in a car escaping from the cops in a high speed chase. The Bat Family flies down to pursue him.
DC Extended Universe
Oswald Cobblepot was born to members of Gotham City's elite and befriended Bruce Wayne. Oswald later went to school in England where he picked up an English accent and joined a nasty gang led by an even nastier man named Simmons when he learned his parents died in a boating accident and lost his inheritance. Oswald would somehow discover his uncle engineered his parent's death out of spite of not being lent money and vow to exact revenge on him and Simmons filled him with knowledge on the underworld and street smarts.
Sometime in 2002 Oswald returned to Gotham City and with his resources built a sizable gang of thieves, killers, drug dealers, hackers and kidnappers. Oswald first found his uncle and killed him. As he expanded his gang he met opposition but came out on top and even challenged Batman on occasion with his wit and strategy. He once came face to face with The Riddler and became harsh enemies. Its rumored upon the disappearance of the metahuman and friend Poison Ivy in late 2007 Penguin captured her and sold her to a 'secret government agency' for immunity in his own city.
After nearly two decades of crime Oswald apparently retired from the game and opened a stylish club called the Iceburg Lounge. However, its revealed he never gave up on crime and is still overseeing his gang's operations without legal troubles whatsoever.
In other media
Holy Musical Batman
The Penguin was one of the rogues who worked with Sweet Tooth to destroy the Batman, and put nuclear Warheads into the city's water supply. At first he didn't like the homicidal candy themed criminal, when he interuppted the Rogues Councils' meeting in destroying the Bat, but after Sweet Tooth killed Chilly Willy with his lollipop to express his villainy, he said, "Ladies and gentlemen, put your flippers together for the NEW king of crime in Gotham." Which resulted in him having some humility.
Trivia
He is only featured in the novelization of the movie. However, he could make an appearance in the upcoming Ben Affleck's and Geoff Johns' The Batman film.
Video Games Gotham Knights Court of Owls (Jacob Kane, Constance Cobblepot & Talons) | League of Shadows (Ra's al Ghul, Talia al Ghul & Man-Bat Commandos) | Gotham City Police Department (Catherine Kane) | Penguin | Harley Quinn | Mr. Freeze | Clayface