The Penguin & The Riddler, from 1960s TV to The Batman

Many of the most famous members of Batman’s Rogues Gallery have already made their on-screen appearances. Starting in 1966 with Batman on television and leading up to the March 4 film premiere of The Batman, there’s never a shortage of DC Comics villainy to plague the streets of Gotham City.

Two super-villains stand out in particular when it comes to the Dark Knight’s infamous adversaries: The Penguin and The Riddler. While they might not employ bone-chilling weapons or the advantage of plant-based super powers, these two enemies give Batman a run for his money — and we all know Bruce Wayne has plenty of that to spare. Ahead of The Batman, let’s take a look at some of the most noteworthy on-screen appearances of The Penguin and The Riddler.

Batman TV Show (1966-1968)

Holy brainteaser, Batman! From a modern perspective, the original Batman television series is a time capsule of bright colors, corny dialogue, and comedic performances. But the TV show will always be notable as the first on-screen portrayal of the Caped Crusader and his Boy Wonder, played by Adam West and Burt Ward. It’s also when Batman’s Rogues Gallery was firmly established, including The Riddler (Frank Gorshin) and The Penguin (Burgess Meredith).

The Prince of Puzzlers, the Count of Conundrums — there are many names to describe Edward Nigma. And as Gorshin portrayed him, this confounding criminal could switch from laughing to menacing in the blink of an eye. On the other hand, The Penguin considers himself to be a cut above the rest. Penguin’s ingenious criminal plans and devious devices often cause the Dynamic Duo to take cover, especially when he uses his many trick umbrellas.

Batman Returns

In 1992, following the success of his first Batman film three years earlier, Tim Burton created a version of The Penguin that is probably his most iconic live-action appearance. Played by Danny DeVito, this version of The Penguin is grotesque — beyond just his scraggly hair and pointed teeth.

As Oswald Cobblepot, DeVito’s Penguin was an outcast. He was abandoned by his wealthy Gothamite parents as a baby, leading him to grow up in the shadows and grime of the Gotham sewers among a horde of penguins. When he crosses paths with Max Shreck (Christopher Walken), a plan hatches in Oswald’s mind to take over Gotham and get his revenge against everyone who wronged him. Watching this Penguin eat a whole raw fish is enough to give you nightmares for weeks.

Batman: The Animated Series (1992-1995)

Between live-action film releases, the critically acclaimed Batman: The Animated Series debuted. Audiences continue to love this series for its distinctive visual style and sophisticated storytelling. Despite being a cartoon, the soundtrack to the show added emotional nuance as well as eerie ambience, plus the creators devised an original animation style known as Dark Deco. This style utilized the darkness that shrouds Batman and his city while also infusing elements of his 1930s noir beginnings.

And when it comes to characterization, the series is still second to none. Each villain has an endless supply of disposable goons. Plus, the super-villains’ relationships to Batman aren’t as simple as “good guy vs bad guy.” The Penguin shifts from sniveling wannabe-aristocrat to capable crime lord and The Riddler’s puzzles went from tricky word games to actual death traps.

Batman Forever (1995)

After Tim Burton left the series, the Batman films took a campy turn. Under Joel Schumacher’s direction, Gotham City adopted bright colors and big personalities, which some fans view with more than a little side eye. However, all things considered, these movies are lots of fun when not taken too seriously. Especially when it comes to The Riddler in Batman Forever.

Alongside Two-Face (Tommy Lee Jones), Jim Carrey’s Riddler terrorizes Batman all across the technicolor city. Carrey takes a page from Gorshin’s 1960s Riddler and really runs with it, transforming the villain into an over-the-top, completely unhinged madman. There’s no doubt he’s a genius, but that genius comes at a price — his sanity. This Riddler will have you questioning more than just his words.

Gotham (2014-2019)

This TV series focused on Jim Gordon, longtime ally of the Dark Knight and eventual Commissioner of the Gotham Police Department. In the series, Jim begins as a GCPD detective who must grapple with the growing threat of organized crime and super-villainy in Gotham. Numerous well-known Rogues Gallery members made appearances on the show with fresh takes on their origins and characterization.

Within these versions, The Penguin (Robin Lord Taylor) and The Riddler (Cory Michael Smith) were closer than ever before. They supported each other’s criminal efforts, uniting against the do-gooders of Gotham. Gradually, their intimate partnership became a source of trust between the super-villains despite their constant backstabbing. Of course, inevitably, they were driven apart by betrayal, causing both men to descend into darker versions of themselves without the other.

Harley Quinn (2019- )

Admittedly, Penguin does not have a very illustrious run in this recent animated series on HBO Max. Staying true to Harley Quinn’s irreverent nature, her solo adventures are a crazed rollercoaster of gore, swear words, and revenge — in other words, a really good time. Harley’s ongoing mission is to break apart the Gotham City Boy’s Club of Villains, led by The Joker but also featuring Penguin and Riddler.

Without giving too much away, Harley gives Penguin the early bird special on a grisly encounter with her bat. Riddler, on the other hand, helps Poison Ivy show Harley she needs to quit The Joker once and for all. Later, Harley captures Riddler and turns him into a glorified hamster stuck running in a giant wheel to power the city. When he escapes, he proves himself to be a worthy adversary against Harley and her squad.

The Batman (2022)

The long-awaited return of the Dark Knight to the big screen will also feature a whole slew of familiar Gotham characters, including Catwoman (Zoë Kravitz), The Penguin (Colin Farrell), and The Riddler (Paul Dano). While details remain hidden in the dark alleys of the city, it’s obvious that these versions of the super-villains will deliver a darkness that’s never been seen before.

No campy outfits, no gothic makeup (except for Farrell’s facial transformation). In The Batman, Riddler and Penguin promise to push Bruce Wayne to his absolute limits. Penguin is a menacing mob boss type and Riddler is an enigmatic presence who terrorizes Batman every step of the way. From the trailers alone, it’s clear they have a chokehold on the city, paralyzing its people in fear. They might even hold the power to uncover Batman’s darkest secrets.

Throughout the decades, Batman and the rest of his Rogues Gallery have adapted, rebranded, and even resurrected themselves over and over again. Some have turned into begrudging allies, and others have remained a thorn in his side. Penguin and Riddler, however, have always stayed true to their core values — maddening villainy and ruthless plots to take down the Bat.

Which versions of The Riddler and The Penguin are your favorites? Let us know in the comments and don’t forget to Let Your Geek Sideshow!