Every Live-Action Version Of The Riddler Ranked Worst To Best

Like every piece of "Batman"-related media, Matt Reeves' "The Batman" has got the world talking. This latest, standalone entry in the DC Comics cinematic canon has delivered on the promises to offer fans a bold new vision for the character's storied lore, and, inevitably, fans have been poring over every little aspect of that vision. Debates about whether the film features the best Batman, the best Catwoman, or the best Penguin are all raging on, among many others. But it can be argued that no character is sparking more conversations than the Riddler.

As the first live-action film to feature the character as a primary villain since 1995's "Batman Forever," "The Batman" has revived public interest in the Riddler and spurred many fans to take another look at his many previous versions. Interpretations of the Riddler have varied dramatically in each of his five live-action depictions, from a social outcast drunk on power to a deranged serial killer to a tech genius driven mad by entitlement and arrogance. But which of those is the best live-action Riddler? Let's go right ahead and solve that particular riddle. 

Better-known for his portrayal of Gomez Addams on the original "Addams Family" TV series, John Astin also showed up on another iconic '60s genre show. In 1967, he was cast as the Riddler on the second season of ABC's classic Adam West-starring "Batman" series, subbing in for the role's original performer, Frank Gorshin.

To this day, there are different explanations floating around as to why Gorshin was replaced. Either he was busy with a gig he couldn't get out of, or he demanded a pay raise that producer William Dozier refused to give. Whatever the truth of the matter, the result was the same: Astin, while a great actor, was pointedly a replacement — and felt like one.

Although he did a fine job with the role on the two Season 2 episodes that featured him, Astin simply didn't have enough time to really make the character his under the shadow of Gorshin's work. Indeed, by the next season, Gorshin had already been brought back as if nothing had happened. Still, Astin did manage to give his portrayal some memorable touches, such as a cane twirl that would later prove an influence on Jim Carrey's take.

"Batman Forever" is not a lot of people's favorite cinematic iteration of the Caped Crusader's mythos, but decades of cultural settlement have made it a significant nostalgia item for Batman fans. And one of the many "imperfect" elements that some fans have grown to have a soft spot for is Jim Carrey's performance as the Riddler.

Heavily influenced by Frank Gorshin's classic turn, this was the first live-action version of the character to get a proper backstory and the first to be referred to by his citizen name of Edward Nygma. On paper, it seemed like the perfect role for Carrey, with a descent-into-madness arc that could play to his strengths as both a comedic and dramatic performer. But the broad, ham-fisted writing didn't tap fully into the things that made the Riddler complex and interesting as a villain — his hubris, his deep insecurity masked by grandstanding, his tremendous intelligence.

Carrey was, therefore, stranded on an island of goofiness, left to carry the character with just his sheer madcap energy and commitment. The performance is highly charismatic and memorable — it's Jim Carrey, after all — but the film's take on the character is subpar.

This is the part of the list where rankings become nearly arbitrary, as every actor has contributed something great and unique to the role. Although the inconsistent writing on "Gotham" led to a few rough patches in terms of character work over the years, the Fox prequel series deserves kudos for deepening and enriching the backstories of some "Batman" villains to a never-before-seen degree. And that was especially true of Cory Michael Smith's Edward Nygma.

This version of Nygma was different from previous Riddlers in that it was presented as a fully-rounded, three-dimensional character, with an engrossing storyline all his own. "Gotham" introduced him as an eccentric, ostracized forensic scientist at the Gotham City Police Department, and, as he began to realize that his intelligence gave him an upper hand on the people who mistreated and belittled him, we got to see him slowly give in to his narcissistic, psychopathic impulses and assume the persona of a full-fledged villain. Smith was an absolute superstar in the role, allowing us to, by turns, empathize with, be terrified of, or absolutely loathe the living daylights out of Nygma. Many "Batman" fans would argue that it was the best-ever translation of the spirit of the comics' Riddler to the screen.

If Cory Michael Smith's Edward Nygma stands tall as arguably the most perfect "orthodox" take on the Riddler, Paul Dano's Edward Nashton is making a splash for the exact opposite reason. "The Batman'"s savvy retrofitting of the Riddler into a terrifying serial killer is the most out-there live-action interpretation of the character yet, but it's so effective, so indelible, that we wouldn't be surprised if it ended up influencing future Riddlers for decades to come.

What makes Nashton such a brilliant villain is that writers Matt Reeves and Peter Craig have honed in on the most essential psychological aspects of the Riddler, and placed them within a context that wholly reshapes them. The core theme of the character's stories has always been power — its pursuit, its exchange, the way it can shift at the drop of a hat. On the most basic level, the Riddler is a man who renders his enemies helpless. "The Batman" understands that disposition for the perfect horror-movie fodder it is, and wrings unspeakable dread out of Nashton's way of messing with Batman, Gotham City PD, and his victims, like a cat playing with a mouse.

On that note, the way the character is integrated into real-world social dynamics is similarly pitch-perfect, his hordes of rabid social media followers mirroring the sense of bottomless despair that today's extremist, cult-mentality-prone internet ecosystem tends to invite. It's not the Riddler we're used to, but it's the Riddler for our times.

It couldn't be anyone but him. As the decades have brought about darker, deeper, emotionally heftier screen adaptations of the Batman comics, the majority of the villains on the lighthearted '60s "Batman" series have been "surpassed" by subsequent versions. That, however, is not the case with Frank Gorshin's Riddler. The actor's take on the character essentially defined the Riddler as we know him, from personality to mannerisms to that unmistakable evil-smartass flair.

In fact, here's how quintessential Gorshin's portrayal was: Before the classic "Batman" show, the Riddler had been mostly relegated to minor, one-off appearances in the comics. It was the runaway success of the character's TV appearances that inspired DC Comics to feature him more and more prominently, eventually turning him into a fixture of the Batman rogues gallery, with inevitable influence from the way he was depicted on the show, as that had been the way audiences came to know him (via Nerdist). It wouldn't be that much of an exaggeration to say that Gorshin is the Riddler.

The success of Gorshin's work earned him a Primetime Emmy nod for Outstanding Performance by an Actor in a Supporting Role in a Comedy (via IMDb), and led to subsequent appearances in the 1966 film spinoff and the 1979 TV special "Legends of the Superheroes." Every Riddler since — whether imitating it, deconstructing it, or subverting it — has been a response to Gorshin's Riddler on some level.