Oswald Cobblepot, also known as The Penguin, is one of the most tragic villains in Batman’s rogues’ gallery. His appearance and horrible upbringing of him forced him to live as an outcast. First appearing in Detective Comics #58 in December 1941, this criminal mastermind and owner of the Iceberg Lounge has gone toe to toe with Batman for the better part of a century.
Being the tragic sad-sack that he is, there aren’t too many comics featuring a victory for Mr. Cobblepot – but there are some. These victories may not be pleasant stories with happy endings and a bow on top, but there are times when Penguin catches a lucky break or manages to snatch a personal victory.
8 Win – Batman: Penguin Triumphant
As its title suggests, Batman: Penguin Triumphant is a one-shot story by writer John Ostrander and penciler Joe Stanton where the Penguin actually gets what he wants, for a time at least. In the comic, the Penguin decides to move into the world of white-collar crime, using new technology to manipulate Wall Street computers. This leads him to previously unknown financial success, putting him in social circles with Bruce Wayne. The Penguin’s biggest triumph comes when he successfully purchases Wayne Manor out from under Bruce Wayne.
7 Loss – Batman: Killing Time
Batman: Killing Time is a newer 6-issue mini-series by industry Batman Tom King and David Marquez. Taking place in Batman’s early days of crime-fighting, the series focuses on a joint operation between Penguin, Riddler, Killer Croc, and Catwoman to break into Wayne Manor and steal some unspecified artifact.
It’s no coincidence that three of the four villains featured in killing time are also in Matt Reeves’ new film, batman. It’s also hardly a surprise when the Penguin is beaten to a pulp by Riddler after handing him his own umbrella. More double-crossing is to be expected, but only time will tell if Penguin gets his revenge from him.
6 Win – Batman Vol. 2 #23.3: The Penguin
Batman Vol 2 #23.3 by Frank Tieri and Christian Duce is part of the New 52’s “Forever Evil” event. In a time when Batman is absent in Gotham City, crime runs rampant. The story begins with Penguin growing angry at a group of scammers winning money at his casino from him. As they mock him, he escorts them outside, demanding they hand over their winnings. The group laughs and claims Penguin has lost his touch from him, not even sending any goons after them. This spurs the Penguin to kill all five men. Laughing at himself, he muses on how he hasn’t killed with his own hands in years.
5 Loss – Joker’s Asylum: Penguin #1
Joker’s Asylum was a series of one-shot stories where the Joker would narrate stories offering origins for some of Batman’s most famous villains. In the Penguin’s issue, written by Jason Aaron and penciled by Jason Pearson, readers are exposed to a young Oswald Cobblepot being bullied by popular girls at his school.
This event sparked his lust for revenge. Later in the story, Penguin falls in love with a slave he’s rescued from human trafficking. Things seem to be going well until she finds the scrapbook where Penguin records all the lives he’s taken or destroyed. Horrified, she tries to leave him, but Penguin uses his resources from her to lock her up and force her back into slavery.
4 Win – Batman: Earth One
Geoff Johns and Gary Frank’s critically acclaimed retelling of Batman’s origin places Oswald Cobblepot in a more central role than is normally seen concerning Bruce Wayne’s transformation into the Dark Knight. In Earth One, Oswald Cobblepot and Thomas Wayne are running against each other for mayor of Gotham City. Although the Waynes are murdered by a random mugger, it was the Penguin who planned to have them killed that day. This launches Penguin to new heights, becoming older and employing the Gotham PD to protect him.
3 Loss – Detective Comics Vol. 1 #58: “One Of The Most Perfect Frame-Ups”
The Penguin’s first appearance is one of his most significant. Detective Comics Vol. 1 #58 depicts Penguin as the crime strategist for a criminal leader known as “The Boss.” When The Boss tries to double-cross him, Penguin kills him with his umbrella and takes over his organization from him. With his new gang of him, he frames Batman for a crime and captures him. However, Robin is able to save Batman and clear his name from him. Penguin escapes on a train, but is unable to defeat Batman, either physically or in the minds of the police.
two Win – Penguin: Pain And Prejudice
The Penguin’s most significant story comes from Penguin: Pain and Prejudice, the longest series starring him as the central figure. Gregg Hurwitz and Szymon Kudranski’s 5-issue mini-series explores the life of Oswald Cobblepot told from his perspective, flashing between his childhood and the present day.
One of the major themes surrounding Penguin is his love for dealing disproportionate revenge against those who wrong him. Someone could look at him the wrong way and find their wife dead the next morning. In the comic, Penguin destroys an entire man’s life just for bumping into him at the Iceberg Lounge.
1 Loss – Penguin: Pain And Prejudice
naturally, Pain and Prejudice does come with its share of pain. In this dark exploration of Oswald Cobblepot’s life, the reader discovers that Oswald murdered his abusive father and bullying brothers so he could become the sole caretaker of his ailing mother. Despite the actions he’d taken from her to grow near to her and all the money he’d amassed from her to give her the best possible life from her, he could not save her. She succumbed to her illness, leaving the Penguin with no reason to care about anyone. Any shred of existing morality vanished then and there.
NEXT: DC: 10 Times The Joker Actually Won
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