A Villain for Every Era: The Penguin and Riddler Have Come a Long Way

The Caped Crusader is back: On March 4, Robert Pattinson will become the seventh actor to don the cowl in a live-action film with The Batman. To prepare, join The Ringer this week as we navigate the grime of Gotham and explore the history of one of the most recognizable superheroes in the comic-book landscape.

Here are a few of the foes Batman faced in his earliest days as a comic book superhero: Hook Morgan and his Harbor Pirates, a spy called “The Brain Burglar,” a golem-like Native American statue (actually a strongman in disguise), Blackbeard (actually a gangster in a pirate costume), a dragon (after Batman and Robin are sucked into a storybook by an experimental machine), the Clock Maker (not to be confused with the Clock King, who wouldn’t make his debut until the ’60s), and the ill-fated Professor Radium. Familiar villains like Joker, Catwoman, and Clayface also made appearances, but reading Golden Age Batman adventures can feel a bit like watching the first rounds of a reality competition show. Many characters are introduced; most don’t have the stuff to go the distance.

Detective Comics no. 58 from December 1941 features the first appearance of Oswald Cobblepot, a.k.a. Penguin, a rotund, dapperly dressed gangster with an arsenal of trick umbrellas. The character’s bird fixation had yet to surface, but the Penguin of 1941 is instantly recognizable as one of the most famous members of Batman’s rogues’ gallery. The same can be said of Riddler—the puzzle-loving criminal most often otherwise known as Edward Nygma—who followed Penguin into the pages of Detective Comics in 1948. While many of their contemporaries in Batvillainy have fallen into obscurity, both Penguin and Riddler have proved resilient, recurring in one different incarnation of Gotham City after another, up to and including Matt Reeves’s new movie, The Batman.

The core elements have remained the same over the years, but the details have changed. Like virtually every long-running comic book character, Penguin and Riddler have evolved, at times radically. The Riddler and Penguin of the Fox series Gotham, with their erotically charged love-hate relationship, bear little resemblance to the characters of, say, the ’60s TV series. In movies, comics, and television shows, the reconsideration of classic villains is often an exercise in how far a character can be bent without breaking. Yet for as much bending as they’ve sustained—and The Batman bends them pretty far—both Penguin and Riddler have been flexible enough to withstand whatever stresses creators have placed on them over the decades.

Why these two have become recurring characters in virtually every version of Gotham City is another matter, a tougher question to answer with this pair than with Batvillain A-listers like Joker (who always works as the chaotic, criminal polar opposite to the staid, law-and-order-loving Batman) and Catwoman (who’s been both an antagonist and love interest since her first appearance). Why should a gangster with aristocratic pretensions and a puzzle obsessive achieve the sort of pop culture immortality denied Mr. Baffle, a character introduced with great fanfare a few issues after Penguin never to be seen again?

Maybe the answer isn’t that complicated. “Comic book characters are 75 percent their look and 25 percent what they say and do,” suggests Glen Weldon, one of the hosts of NPR’s Pop Culture Happy Hour and author of The Caped Crusade: Batman and the Rise of Nerd Culture. Amid a sea of standard-issue 1940s gangsters, Penguin, Riddler, and a few other future Rogues Gallery fixtures stood out. They also benefited from writers and artists with a flair for running with colorful characters once they found a winning concept, who seemingly understood that they could do more with Penguin than characters that looked like also-rans from the jump.

The names of those creators, however, couldn’t always be found in the comic books on which they worked. Though Bob Kane, billed for many years as the sole creator of Batman, would take responsibility for creating both Penguin and Riddler, the real credit, as with all things Kane, lies at least partially elsewhere. Since 2015, any piece of media featuring Batman has included a credit reading “Batman created by Bob Kane with Bill Finger,” a change to the long-standing practice of listing Kane as the sole creator. Finger’s role in shaping Batman was an open secret for years, but wasn’t formalized until author Marc Tyler Nobleman made a push for it with his 2012 book Bill the Boy Wonder: The Secret Co-Creator of Batman. The same kind of credit-grubbing and spotty record-keeping has made the stories behind the creation of other Batman characters similarly murky, but all evidence suggests much of the credit should again fall to Finger, remembered by those who knew him as a slow writer who was nonetheless a font of ideas and concepts. Finger kept what he called a “gimmick book,” Nobleman says, “a notebook with random facts or tidbits he picked up along the way that he could use as a reference. He always had a wealth of options at his fingertips.”

For Penguin, the inspiration seems to have been pretty direct. Though Kane, who drew Penguin’s first appearance from a script by Finger, claimed to have been inspired by the cartoon penguin that once served as the mascot for Kool cigarettes, Willie, Finger spoke of seeing resemblance between emperor penguins and stuffy English gentlemen. Per Nobleman, the latter seems more likely. “Whenever there’s a dispute between what Bob and Bill said, obviously I’m going to go with Bill because he didn’t have a history of lying,” he says. Whatever the source of his appearance, his personality has been just as key to the character. Cobblepot’s origin story varies with each new retcon and new universe in which he appears: sometimes he’s a seedy thug in high-class clothes; sometimes he’s a son of privilege gone bad; often he’s a criminal with political aspirations. But the anger and arrogance Finger breathed into him has remained consistent.

Even less is known about the creation of Riddler, who first appeared in a 1948 issue of Detective Comics in a story written by Finger and drawn by Dick Sprang. Nobleman points out that longtime DC Comics editor Julius Schwartz gave Finger full credit for the character’s creation in a 1965 letter column, seemingly ignoring what Kane was still claiming at the time. Schwartz seems to have reached the same conclusion as Nobleman, decades earlier. Though the character can sometimes be used as a kind of bargain-bin Joker, the best treatments of Riddler have stayed true to the character’s obsession with proving himself to be the intellectual superiority of everyone he meets—especially Batman.

For a swath of Batman’s history, it looked as though these two enduring antagonists might not endure. Riddler first appeared near the end of what would come to be known as superhero comics’ Golden Age, made one encore appearance, then disappeared after the story ended with him behind bars. He sat out a tough stretch for caped heroes and their bad guys. Superheroes waned in popularity in the 1950s, a decade that often found Batman (and an ever-expanding Bat-family that stretched to include the magical imp Bat-Mite and the faithful Ace the Bat-Hound) in whimsical science fiction and fantasy stories rather than battling criminal masterminds. (The decade’s moral panic over hard-edged comic book content didn’t help.) Penguin made only a handful of appearances in the Eisenhower era. Riddler fared even worse, disappearing for 17 years until making his return in 1965 as part of a movement to bring Batman’s adventures back to their roots. Both villains’ profiles would soon get a boost on a previously unimaginable scale, however.

An instant sensation when it debuted in 1966, the ABC TV series Batman helped make Batman’s foes household names and defined their personas in the public consciousness. Veteran actor Burgess Meredith keyed into the aggrieved, aristocratic aspects of Penguin’s personality while creating a distinctive, bird-inspired speaking pattern. A deft performance from a veteran actor who never treated it as an act of slumming, it’s silliness with a menacing edge. There’s an edge, too, to Frank Gorshin’s interpretation of Riddler as a criminal driven as much by obsessive mania as greed. Leaving aside John Astin’s two-episode stint subbing in for Gorshin, these versions became the definitive interpretations of the characters for a generation. In some ways they still are, serving as the iconic starting point that subsequent incarnations would either pay homage to or react against, but never ignore.

That doesn’t mean the characters themselves didn’t experience some lean years. With the fading of the Batmania that gripped the nation in 1966 and the cancellation of the Batman television series after a three-season run, the comics began to favor darker, more grounded stories that eschewed the canted angles and bright colors of TV’s Gotham City in favor of noir-inspired shadows and deadlier foes. Joker easily fit into this new, darker world, which had plenty of room for a homicidal clown—but Penguin and Riddler spent years operating mostly on the margins. They could often be seen on Saturday morning as antagonists on Super Friends but only rarely in the comics themselves.

After Frank Miller helped redefine Batman with a pair of mid-’80s stories set on opposite ends of Batman’s crime-fighting career—the origin story Batman: Year One and The Dark Knight Returns, which depicts a middle-aged Batman coming out of retirement—they didn’t fare much better. Miller helped usher in an era of grimness and grit even further removed from ’60s camp than the comics of the 1970s. Stripped of his tux, Penguin spent some time in the Suicide Squad before returning to Gotham to resume his life of crime. The Riddler reappeared in a 1990 story that found the character going to previously unimaginable extremes, kidnapping babies as part of a riddle-themed criminal scheme; even shoving a ping-pong ball down one’s throat and forcing Batman to perform an emergency tracheotomy.

While both struggled to find their place in the new Batman order, neither was ever in much danger of disappearing in the 1990s, particularly after some boosts from other media. On television, Batman: The Animated Series created a version of the Batman universe that mirrored the clean line art style favored by series cocreator and chief character designer Bruce Timm. The series pared the classic characters down to their essential elements—Penguin behaves like an arrogant thug with an arsenal of deadly umbrellas; Riddler acts as a malevolent trickster determined to foil the World’s Greatest Detective—and discovered they could carry stories that fit into a dangerous, shadow-drenched (if kid-friendly) Gotham City. Elsewhere, on the big screen, Tim Burton reworked Penguin into a sewer-dwelling grotesque (played by Danny DeVito under heavy makeup) in Batman Returns and Jim Carrey turned Riddler into, well, Jim Carrey in Batman Forever.

A decade of TV and movie appearances helped secure the characters’ places in Batman lore, both as part of Batman’s past and his future. In the comics, Penguin ascended to the top of Batman’s underworld (though his position has occasionally been challenged) while Riddler has emerged as a foe whose intellect makes him an even match with Batman. Apart from a period in which he went straight and worked as a private detective (it didn’t last), he’s served as a mastermind in memorable story lines like Jeph Loeb and Jim Lee’s early-’00s “Hush” and Scott Snyder and James Tynion IV’s “Zero Year,” a year-long story arc in which a just-starting-out Batman tangles with a mutton-chopped Riddler for control of the city itself.

This is all, of course, just a sampling of stories featuring the characters. One would need to scan dozens of overstuffed wiki pages to chart the ups and downs of Penguin and Riddler over the years. (They’re out there, if you want to read them.) Yet, despite the years of story lines, retcons, and minutia, in some ways it’s easier to explain where Penguin and Riddler come from and what they’ve done than why they’ve stuck around. “For all the iconographic power he has today,” Weldon says, “the Penguin is really a mishmash of a lot of different things that don’t go together. Penguins and umbrellas: it seems like they go together, but they really don’t. … Ultimately, he’s just a crook in gentleman drag.”

But maybe that’s explanation enough. Penguin draws Batman into the world of crime fiction. The Riddler, on the other hand, opens up other storytelling possibilities as a foe who’s Batman’s intellectual equal, a kind of Moriarty to his Sherlock Holmes. “Riddler plays directly into the detective aspect of Batman,” Weldon says. “There aren’t many other characters that do that to the same extent.” It’s Batman’s ability to serve many different types of stories that have kept him alive for over 80 years—and to show off that versatility, he’s needed foes who challenge his various strengths.

Though invariably on the second tier of any list of Batman’s best opponents, Penguin and Riddler have evolved from opponents who drop in and out of Batman’s life to essential elements to Batman lore that can be tweaked to serve the needs of any given Batstory. Riddler brings deadly puzzles and Penguin brings a touch of sadism to the popular trilogy of Arkham video games. In Gotham, the performances by Robin Lord Taylor and Cory Michael Smith as Oswald Cobblepot and Edward Nygma, respectively, fit nicely into the series’ gallery of twisted and murderous but sometimes uncomfortably human supporting characters.

While neither Christopher Nolan nor Zack Snyder found a use for them, it’s not surprising to see both Cobblepot (Colin Farrell) and Edward (Paul Dano) popping up in Matt Reeves’s The Batman. These versions may not much resemble the characters introduced in the 1940s at first, but they are both variations on basic ideas ripped from Bill Finger’s notebooks. Farrell’s Penguin has unrefined manners but his anger, aspirations, and attire mark him as Penguin in more than just name (as do the prosthetics that give Farrell the beakish appearance that’s become synonymous with the character since DeVito). As Riddler, Dano embraces the madness of a character who’s compelled to invite others to unravel the code by which he operates. Any resemblance to the Zodiac Killer, Son of Sam, or other real-life serial killers who made taunting the public part of their MO is no accident, but the parallels also tease out aspects of the character that have been there from the start. The elements have changed to reflect the times around them, but the characters’ frameworks, however unexpectedly, have proved they’re built to last. Hook Morgan and his Harbor Pirates could never say that.

Keith Phipps is a writer and editor specializing in film and TV. Formerly: Uproxx, The Dissolve, and The A.V. Club.