1
“One of the Most Perfect Frame-Ups,” Detective Comics #58 (1941)
The Penguin stood out from many Batman baddies, right from the very beginning. Written by Bill Finger, penciled by Bob Kane, and inked by Jerry Robinson and George Roussos, “One of the Most Perfect Frame-Ups” is a solid early caper. The story introduces the Penguin as a well-dressed crook who steals expensive works of art and sells them on the black market via a fence. That is until the fence tries to double-cross the Penguin, who ten does away with the boss and sets himself up as a new criminal force.
The story finds the creative team at its best, with Kane’s Chester Gould-inspired cartooning giving the Penguin a distinctive look, especially when highlighted with Robinson and Roussos’s inks, and Finger crafting a propulsive tale. Between the Penguin’s trick umbrellas and jovial nature, “One of the Most Perfect Frame-Ups” stands as a strong Batman story, beyond the villain’s initial appearance.
2
“Love Bird,” Batman Annual #11 (1987)
By 1987, the Penguin had gained his civilian identity Oswald Cobblepot, but otherwise seemed caught in the past. As Bronze Age writers tried to tell gritty Batman stories, they couldn’t find a place for the Penguin and his trick umbrellas. “Love Bird” from Batman Annual #11 serves as a rare exception to the habit of leaving Penguin penned in.
“Love Bird” comes from writer Max Allan Collins and artist Norm Breyfogle, who present a Penguin who gets out of prison on bail, prompted to reform because of his love for a woman called Dovina. Although Collins writes Batman as a harsh disciplinarian, the rest of the tale—and Breyfogle’s cartooning—keeps things fun and light.
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3
Batman: Penguin Triumphant (1992)
Released in conjunction with Danny DeVito’s performance as a disgusting Penguin in Batman Returns, Batman: Penguin Triumphant gives Cobblepot his own modern-age revision. Writer John Ostrander, penciler Joe Staton, and inker Bob Smith keep Oswald’s pointy nose and round body shape from previous incarnations, but they give the Penguin a new mission.
After hearing a TV psychologist speculate about what he could be if not obsessed with Batman, the Penguin decides to reinvent himself as a legitimate businessman. The story brings Oswald into the orbit of Bruce Wayne and other members of respectable society but reminds the reader that he’s still the insecure and spiteful man he’s always been. The combination sets the stage for Penguin tales to follow, positioning him as a unique antagonist who walks a blurry legal line.
4
“Cracks,” Showcase ’94 #7 (1994)
The anthology series Showcase ’94 gave creators the opportunity to tell standalone stories with characters who don’t always get the spotlight, making it the perfect venue for a new Penguin adventure. Writer Peter David and artists P. Craig Russell and Michael T. Gilbert show a side of the Penguin rarely seen: his criminal genius.
“Cracks” takes place almost entirely in the Gotham PD interrogation room, where Commissioner Gordon tries to get the Penguin to reveal where he’s trapped Batman. Thanks to its limited scope, “Cracks” focuses on the game of mental cat and mouse between the two. Yet the art by Russell and Gilbert keeps things playful, making for a satisfying Batman story, even if Batman is missing.
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5
“The Penguin Returns,” Batman #548 – 549 (1997)
“The Penguin Returns” feels almost like a sequel to Batman: Penguin Triumphant, checking in on Cobblepot’s life as an honest man. Where Penguin Triumphant saw the title character trying to go legit, he’s now bored to death in “The Penguin Returns.” No longer satisfied with running the Iceberg Lounge and overseeing the Gotham underworld, Penguin returns to his roots, embarking on bird-based crimes.
“The Penguin Returns” boasts a super team of writer Doug Moench, penciler Kelley Jones, and inker John Beatty, who tell the story with all the drama one wants from a ‘90s Batman story. The creative team balances the darker, more extreme nature of Batman tales in the Modern Age. But, in keeping with the story’s throwback nature, “The Penguin Returns” retains a sense of Golden Age fun.
6
“Bread and Circuses,” Batman: Legends of the Dark Knight #117 and Batman: Shadow of the Bat #85 (1999)
“Bread and Circuses” takes place during the No Man’s Land storyline, one of the most epic undertakings in DC Comics history. After a massive earthquake levels Gotham in the Cataclysm storyline, the Federal Government declares the city condemned, leaving Gotham in ruins. As its title suggests, No Man’s Land sees Gotham fall into chaos, with each of the villains and heroes establishing their own territory.
In “Bread and Circuses,” writer Ian Edginton and artist D’Israeli check in on the Penguin, who has set up an exclusive club in the ruins of Gotham. In his newly designed Iceberg lounge, the Penguin enjoys the respect and power he always wanted, lording it over those who cannot let go of the lush life they once lived. And that presents a new challenge for Batman, who tries to keep his city together.
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7
The Penguin: Pain and Prejudice (2011 – 2012)
As this list demonstrates, creators have been trying to make the Penguin a darker character since the end of the Bronze Age. That impulse hits its peak with The Penguin: Pain and Prejudice, a five-part miniseries from writer Gregg Hurwitz and artist Szymon Kudranski.
Pain and Prejudice has a fairly thin narrative, split across two timelines. In the present storyline, Oswald woos a blind woman who cannot see his physical irregularities and admires what she considers his kind strength. In the past, the child Cobblepot vies for his mother’s affection, separating her from his brothers and father. Hurwitz and Kudranski lean into the darker aspects of the Penguin’s story, reveling in his sadistic cruelty. It’s not to everyone’s taste, but for anyone who wants edgier Penguin tales, Pain and Prejudice is for them.
8
DC Comics The Penguin: Pain and Prejudice (2011 – 2012)
Instead of making the Penguin meaner to make him appeal to modern readers, writer John Layman and artist Jason Fabok just get rid of Oswald Cobbelpot altogether. In “Emperor Penguin,” one of Cobblepot’s tall and handsome thugs tries to supplant his boss, establishing himself as the Emperor Penguin.
Of course, Oswald won’t give up the title without a fight. “Emperor Penguin” in part serves as a referendum on the Penguin as a character, showing the reader why he works best as the traditional short guy with a long nose, a guy who chooses to fight with trick umbrellas and not flashier weapons. There’s a reason that the Penguin has plagued Batman for decades, and it’s all laid out in “Emperor Penguin.”
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9
“Prodigal Bird,” The Penguin #1 – 6 (2023 – 2024)
Tom King’s planned 100-issue run on Batman, which got truncated after backlash to the storyline in which Selina Kyle leaves Bruce Wayne at the altar, remains divisive and compelling. King’s thoughtful, philosophical approach challenged readers’s expectations for Batman and his rogues gallery.
King brings that same sensibility to his work on the ongoing book The Penguin, starting with the “Prodigal Bird” storyline. Made with artist Rafael De Latorre, “Prodigal Bird” spins out of the main Batman book, in which Cobblepot has faked his death and retired to run a small shop. But when his children embark on their own plot, Cobblepot must return to his Penguin identity—with Batman as his partner.
10
DC Comics Batman: The Long Halloween (1996 – 1997)
While promoting his upcoming series Batman: The Last Halloween, writer Jeph Loeb opined that, outside of the aforementioned series from Tom King, no one has told a great Penguin story. This list disproves his claim, but even if he was correct, Loeb would have been part of the problem. After all, while Cobblepot gets some attention in The Last Halloween, the Penguin only plays a small role in the two previous chapters of the story, Batman: The Long Halloween and Batman: Dark Victory, which Loeb made with the late, great artist Tim Sale.
The Penguin’s omission is all the more glaring given the great influence that The Long Halloween has had on popular culture. The 13-part series puts Batman on the trail of the Holiday Killer, who targets members of the Falcone crime family, including daughter Sofia. Set at the start of Batman’s career, the tale shows how costumed villains take over Gotham’s criminal world, a story that informed The Dark Knight, The Batman, and, by extension, The Penguin.