Don’t let the Penguin’s often amusing appearance fool you, he is easily one of Batman’s most dangerous foes. While many might be visually disarmed by his short stature, tuxedo and umbrella motif, Oswald Cobblepot is a true bird of prey. As we prepare for Colin Farrell’s portrayal of Cobblepot in Matt Reeves’ The Batman, let’s take a look at the Penguin’s notorious rap sheet.

First Impressions

The Penguin first appeared in 1941’s Detective Comics #58, and his first scene wasn’t very flattering.  Bruce Wayne and Dick Grayson spotted him at an art exhibit, and Bruce told Dick to hurry along because it’s not polite to laugh at someone’s appearance. Ouch.

That’s pretty harsh, but Penguin soon proved that appearances can be deceiving. He robbed the art exhibit right under Bruce’s nose, and even worse, he was able to frame Batman for the robbery, convincing the police to arrest the Caped Crusader. Of course, Batman was able to clear his name and recover the Penguin’s stolen goods, but it was still an impressive first outing for the gentleman criminal.

Oswald Origins

Readers didn’t learn that Penguin’s real name was Oswald Chesterfield Cobblepot until a 1946 Sunday newspaper strip. From that point on, Bat-fans knew his real name, but his origin wasn’t explored until 1981’s The Best of DC #10. The story revealed that Oswald always carries an umbrella because of his overly cautious mother. Oswald’s father had died of pneumonia, and ever since then Mrs. Cobblepot pestered her son about never leaving the house without one.

His love for birds came from the family bird shop, and the name Penguin—well, let’s just say kids could be cruel. 1989’s Secret Origins Special #1 revealed that a kid nicknamed Sharkey was the first one to call Oswald “Penguin,” and Cobblepot caught up to him as an adult and made him regret that decision. Penguin: Pain and Prejudice updated Oswald’s story to reveal that he was bullied by his older brothers—that is until he murdered them all one by one. Suffice to say, Penguin has always been somewhat of a bad bird.

From Colorful Criminal to Deadly Mobster

Penguin has an interesting role in the hierarchy of Gotham villains. He fits right in with costumed criminals liked the Joker and the Riddler, but he also is at home among Gotham mobsters like Carmine Falcone and Sal Maroni. In many ways, Penguin is like an emissary between the two worlds of Gotham’s underworld, but it wasn’t always that way.

For most of his early appearances, Penguin committed bird-related crimes using umbrella and bird-related gimmicks. However, Penguin set himself apart from his criminal colleagues by fashioning himself as a high society conman. Oswald dressed nice and committed what he felt were smart and sophisticated crimes.

The beginnings of Penguin’s transition from colorful rogue to grounded mobster can be seen in John Ostrander and Joe Staton’s classic 1992 graphic novel Penguin Triumphant. During the story, Oswald Cobblepot becomes a corporate criminal, manipulating the stock market while pretending to be a “legitimate businessman.” He begins rubbing elbows with Gotham’s elite, and Bruce Wayne is none too pleased when he starts seeing Oswald at high society events. Penguin is caught and imprisoned at the end of the comic, but this caper can be seen as the dry run for the Penguin’s next big endeavor.

In Detective Comics #683, Oswald Cobblepot is seen operating a nightclub called the Iceberg Lounge, and the establishment has become a defining part of his character, possibly bigger than his umbrellas. (Look for it in The Batman.)

The Iceberg Lounge is a cover for a series of illegal activities, from smuggling to arms dealing to human trafficking. It’s given Penguin what he’s wanted since his first appearance—power. At the Iceberg Lounge, he’s the undisputed king, and it’s a reign that’s both noticed and respected by Gotham City’s many crime lords. Despite this change, he’s not above working with folks like the Joker or Scarecrow. Just don’t expect him to join them at Arkham once the caper is done.

Mayor Cobblepot

Ever since 1966, the Penguin has had an obsession with Gotham City Hall. Oswald Cobblepot has run for mayor of Gotham City numerous times across different continuities in the multiverse. The first example was in the 1966 Batman television show, where Penguin ran a crooked campaign for the office. His opponent was Batman (naturally), which led to one of the goofiest televised debates in the history of politics, and that’s saying a lot.

Penguin also had a failed mayoral campaign in the 1992 film Batman Returns. Cobblepot was a puppet candidate for a mogul named Max Shreck, who wanted a mayor he could keep in his pocket. In the end, the electorate turned on Penguin after Batman played some unflattering audio of Oswald trashing his voters.

During the third season of Gotham, Penguin ran for mayor and actually won, but his tenure in city hall was cut short thanks to a war between him and the Riddler. Oswald also won Gotham’s mayoral election in Batman Adventures (a comic series set in the continuity of Batman: The Animated Series), but it turned out that Clock King had rigged the election for him. More recently, Cobblepot was also depicted as mayor in the graphic novel Batman: Earth One.

In mainstream comics continuity, Oswald’s quest to capture city hall didn’t begin until 2013. During a city-wide villainous takeover, Oswald declared himself mayor of Gotham, but Batman put a stop to that in Forever Evil: Arkham War. He ran a more legitimate campaign in Catwoman: Election Night, but the Dark Knight stopped that one as well.

In short, Oswald Cobblepot wants city hall, no matter what world of the multiverse he’s on.

Penguin in Love

Oswald Cobblepot might have a great deal of hatred in his heart, but there is also a little bit of love. Unfortunately, his life as a master criminal often gets in the way of any romance.

In Superman’s Girlfriend Lois Lane #70, Penguin proposes to Catwoman, who pretends to accept before attacking him. (It turned out that Catwoman was really Lois Lane in disguise, which technically means that Oswald Cobblepot was engaged to Lois Lane for a few seconds in the Silver Age.) In Batman Annual #11, Oswald decided to give up his life of crime to marry Dovina Partridge, a woman he had been writing love letters to from prison. Sadly, Dovina wasn’t seen after her debut appearance, and it can be assumed that Penguin’s relapse into criminal life ended their engagement.

In Gotham season three, Penguin fell in love with the Riddler, but his jealousy destroyed any hope of a relationship. When Nygma began dating a woman named Isabella, Oswald planned her murder in order to clear the field. Riddler found out and things spiraled from there.

Oswald began romancing a blind woman named Cassandra during the Penguin: Pain and Prejudice limited series. Oswald worked hard to hide his criminal lifestyle from Cassandra, and worked even harder to keep her from touching his face, afraid she wouldn’t like his true appearance. Unsurprisingly, this relationship ended both shockingly and tragically. After Cassandra succeeded in tenderly touching Oswald’s face, the Penguin stabbed her before she could reject him. Her final words were marveling at how lovely Oswald’s face was.

Penguin Actors

Although the Penguin has been around for over 80 years, Colin Farrell is only the fourth actor to portray him in live action. Burgess Meredith was, of course, the first person to bring Penguin to life on screen in the 1966 Batman television series and spin-off movie. Meredith’s performance included an iconic squawk-laugh hybrid that made its way into the comics. Amusingly, Meredith reprised his role as the Penguin in a brief cameo on The Monkees television series, which raises lots of questions about how big the DC Universe really is.

Danny DeVito played a menacing version of Oswald in the 1992 film Batman Returns. DeVito’s Penguin had been abandoned by his parents as an infant, which led to him angrily lashing out at the world. Leading a gang of violent circus performers, Penguin terrorized Gotham City before Batman put a stop to him.

Robin Lord Taylor played an earlier version of Penguin on the small screen in Gotham. Oswald Cobblepot started out as a low-ranking umbrella boy for the mobster Fish Mooney, but by the end of the series, he was the kingpin of Gotham’s underworld. Taylor’s performance brought depth and sympathy to Cobblepot, as viewers watched him experience love, loss, triumph and tragedy. Some would argue that Gotham was just as much a Penguin origin story as it was one for Gordon and Batman.

Now, it’s Colin Farrell’s turn to hold the umbrella, and what a deadly umbrella it is. Penguin is unpredictable, violent and cunning…and there’s no telling just what kind of trouble Farrell’s version of Oswald will bring to the table.

The Batman, directed by Matt Reeves and starring Robert Pattinson, Zoe Kravitz and Colin Farrell as the Penguin, is in theaters on March 4. Be sure to check out our official movie page for all the latest news, articles and videos.

Joshua Lapin-Bertone writes about TV, movies and comics for, is a regular contributor to the Couch Club and writes our monthly Batman column, "Gotham Gazette." Follow him on Twitter at @TBUJosh.