10 Best Penguin Storylines from the Comics, Ranked

With the success of the recent hit MAX drama The Penguin, fans are likely jumping to DC’s catalog of comics to further pursue interesting stories about Gotham’s Gentleman of Crime—but a character with such a rich history needs guidance as to where to start.

While the easiest option may appear to be Tom King’s recent The Penguin maxiseries, having just ended in September of this year, the villain has had plenty of other, arguably better, stories across the years. From event tie-ins to older one-shots to his own miniseries, Penguin’s stockpile of stories is as great as any of Gotham’s other villains.

Out of all of Batman’s villains, the Penguin is known to be a cruel and heartless foe, which makes his sparse moments of humanity all the more surprising. They’re few and far between, but earlier eras of the character—long before he was as viciously vindictive as he is today—emphasized some of his softer tendencies.

Batman Annual #11 was dedicated to the love stories of two Batman villains: Preston Payne—A.K.A. Clayface III and The Penguin. While the latter’s tale didn’t take up the whole issue, it followed Cobblepot’s efforts to leave crime behind so he could pursue a relationship with a woman who held a similar interest in birds. An issue that made readers root against Batman’s paranoia for once, it was a sweet story that stands out from the villain’s more tragic romantic endeavors in later comics.

The early ’90s were the final days of the classic iteration of Penguin, a gentleman thief with eccentric dreams and even more out-there plans. “The Penguin Affair” was one of the greatest of these stories, a three-parter that showed one of the villain’s most ambitious schemes to date while fleshing out a minor—though compelling—future Batman ally.

Penguin found and recruited the lost Harold Allnut as he wandered the roads to Gotham, seeing past the deformities others harassed the man for and utilizing his genius mechanic ability. In a plan that seemed like an homage to Alfred Hitchcock’s The Birds, Cobblepot used Allnut’s engineering prowess to command a large flock of birds to terrorize Gotham at his whim. To date, it’s been the best example of Oswald’s bird-themed crimes, showcasing his infamous losing streak with his romantic life.

While stories such as “The Penguin Affair” and Batman: Penguin Triumphant were turning points in Penguin becoming more of a shrewd, business-oriented crook, “The Return of the Penguin” was the final farewell to his time of flighty crime. After having retired for a few years, boredom started catching up to Oswald Cobblepot, so he wished to have his time in the sun again.

To get his kicks, he would go on a small crime spree, taunting both police and Batman in the process. He left clues indicating that it was he who stole various artifacts or killed criminal competition, but he planned everything out so that he could not legally be held accountable for any of these crimes. It was his final farewell to engaging in crime directly before taking over the Iceberg Lounge once more, content in having “lived” once more.

7 Penguin Could Always Calculate The Odds

The Iceberg Lounge is an iconic fixture of Gotham and has appeared in almost every Batman adaptation that saw it fit to include the Penguin. Still, it’s a rather recent addition to the world of Gotham, having only been created in 1995 as part of the “Odds Against” and “Darkest Day” two-parter.

Here, the Lounge became Penguin’s permanent base of operations, a safe space for him to conduct his illegal operations. While the story isn’t the most profound, it’s fun to detail the villain’s plans by recruiting an actuary and planning a series of robberies in broad daylight to try and outsmart Batman. These endeavors would go south, but as usual, Cobblepot would sway the situation to his advantage to keep his hands clean.

6 No Man’s Land Was A Fun Outing For Penguin

One of the greatest events in Batman’s history, No Man’s Land was a sweeping epic that showed how Gotham would respond to a devastating natural disaster. It was a unique event because it was more of a status quo than a specific threat, not an issue that could be resolved through punches and kicks. Gothamites would have to survive the impact of the earthquake, which led them to be cut off from the rest of the USA.

Funnily enough, one of the few characters who did good for himself during this time was the Penguin. He was able to have his men evade the blockades surrounding Gotham, allowing items to be shipped in and out. The Iceberg Lounge was not only his base of operations but also a trading hub for the desperate to try and garner supplies. While Cobblepot wasn’t the main focus of No Man’s Land, he was a critical player in the politics between the different factions of the time, one whose cunning was put on great display in a great handful of issues.

5 One Bad Day Was An Empowering Underdog Story

One Bad Day was a series that aimed to give some of Gotham’s greatest villains one-off stories in the vein of the infamous comic Batman: The Killing Joke. Guaranteed a spot due to his iconic status among the rogues, Penguin’s issue was the third in the series—and after two particularly weak stories about The Riddler and Two-Face, Penguin came in with a much stronger tale.

Oswald Cobblepot’s status as an underdog is key to his story, and One Bad Day: Penguin had fun with this idea by building a story off of it. Oswald had been ousted from his position of power by an underling known as the Umbrella Man and had to claw his way back up to the top with minimal resources, a silver tongue, and a bit of luck. The story also showed what simmered beneath Penguin’s refined airs and charms, that he had animalistic tendencies waiting to leap out at the right moment.

4 An Interval Issue Showed How Penguin Dealt With So-Called Bullies

The New 52 had many one-shots dedicated to fleshing out many supervillains, part of the buildup to the Forever Evil event, appearing as decimal-numbered issues in-between the primary issues of series like Batman. As would be expected, many of Batman’s villains got their own one-shots, Penguin among them.

While some of these stories were hasty origins for these villains, others showcased them in their prime. “Bullies” chose to tell a story about the latter, the Penguin having established himself as the top dog in Gotham once more after doing away with the Emperor Penguin character. But the state Governor wished to begin a crusade against Oswald, despite their past as friends from school, and the villain couldn’t tolerate such a grievous offense. The story is short but sweet, showcasing the Penguin’s brutal nature and hunger for power in an efficient way.

3 Penguin Triumphant Started A New Era For Penguin

Penguin has had two major eras that defined his character. He began as a gentleman thief with an overt bird gimmick before slowly transitioning to the role of a mobster dealing with white-collar crime. This transition between the two eras primarily occurred in the 1990s and was assisted by a one-shot created to promote Batman Returns.

Batman: Penguin Triumphant presented a fun story in which the Penguin decided to give more respectable crime a try and was enthused with the results. He shed the veneer of being a gentleman thief and took on the guise of a legitimate businessman, all the while using the talents of an old friend and a computer program to manipulate Wall Street and, thus, the stock market. While Cobblepot would eventually grow bored with this easy lifestyle, the story was the first of many that cued the future direction of this character.

2 He Who Laughs Last Was A Tragic Romance

The Joker’s Asylum series was one of the first anthology titles dedicated to giving Gotham’s villains their own one-shots, a precursor to the Eisner darling series One Bad Day. Among the first wave of this series was a special all about Penguin, titled “He Who Laughs Last.” The story dealt with Oswald’s childhood, the bullying he faced, and his violent manner of retaliating, but it was primarily another attempt at giving him a short-lived romance.

Penguin bought a woman named Violet from a human trafficker to rescue her, and the two seemed to truly connect and fall in love with one another. But once Violet caught a glimpse of Oswald’s true colors, she tried leaving him, only to be returned to the hellish conditions from which she thought she had escaped. The one-shot was built on how Penguin’s petty range can cause him to even lash out against people or things he cares about because, to him, any perceived slight is grievous.

1 Pain and Prejudice Is The Definitive Penguin Comic

There has been a recent uptick in Batman villains getting solo comic series, some lasting longer than others. Before Tom King’s 2023 The Penguin series, there was 2011’s Penguin: Pain and Prejudice by Gregg Hurwitz and Symon Kudranski. The series took time to flesh out Gotham’s Gentleman of Crime in a way that hadn’t been seen before, dedicating five whole issues to spotlight him. Every detail of Penguin’s life and personality was spelled out for readers.

His fixation on his mother, who truly did love him, how he disposed of his brothers and father, his insecurities going so deep that he’d ruin the life of anyone who laughed at him, his origins, and so on. This was all set alongside one of many schemes to defeat Batman, and surprisingly? A love story with a blind woman named Cassandra, doomed to end in tragedy like all his other relationships. The series is a breezy must-read for anyone interested in the Penguin, blending elements of the character, both new and old, to craft a definitive story.