Batman has one of the best rogues galleries in the history of comic books, from the Joker to Bane, to Scarecrow, each of his adversaries brings something important to the story. One of the most varied of Batman's cast of villains is The Riddler, who has been as silly as he has been terrifying and has recently undergone his fourth ever live-action iteration.

The Riddler is not the most iconic Batman villain, that title still probably goes to the clown, but he is one of the most intriguing in all his different portrayals. Between the four unique live-action adaptations, each era of Riddler's depiction in comics has made it to screens.

Updated on March 17, 2022 by Joshua Kristian McCoy: Now that Matt Reeves' hit adaptation of the beloved character has hit the screen, the list needs to reflect his grand arrival. Paul Dano represents the fifth actor to portray the character in the fourth narrative universe. Reeves' version of the character takes a little inspiration from the comics, a little more inspiration from the films, and a ton of inspiration from real crime and killers. The character has evolved in this new version, along with his endless new ideas in the comic books. Whether he reappears in this film franchise or another, it will be interesting to see how any Riddler handles following Paul Dano.

RELATED: Zack Snyder Reveals The Batman Villains He Wanted To Bring To The DCEU

The Comics

Riddler tipping his hat Cropped

The Riddler, AKA Edward Nygma, was created by Bill Finger and Dick Sprang in 1948. Edward is obsessed with puzzles of all kinds and delights in turning his criminal activities into battles of wit between himself and the law. He believes himself to be more intelligent than anyone in the world and, when he meets Batman, he devotes himself to outsmarting the Bat.

Riddler's motivation shifts often, but he is great fun when he singularly focuses on his duel with Batman. He has been depicted as a sane but nefarious prankster, a criminal with a debilitating obsession with leaving behind clues, and as a Zodiac-style serial killer. There are several works in which he either never or rarely appears, but his influence is still important, like the Riddler Trophies in the Batman: Arkham game series.

Batman (1966-1968)

60s-riddler Cropped

The first live-action iteration of the Riddler occurred way back in 1966, as one of many villains in the first Batman series. As most fans know, the Adam West series was a silly action romp, where Batman and Robin cartoonishly beat down bank robbers with big animated sound effects. The Riddler of this series was portrayed by Frank Gorshin for the first and third seasons, and by John Astin in the second. This depiction of the character is based on his appearance in the DC's silver age when the Comics Code Authority held sway and heavily restricted comic books. In the first season, Riddler appeared more times than any other villain, and Gorshin won an Emmy for his performance. It was this series that made Riddler a more central fixture of the Batman mythos.

Gorshin's Riddler fits the 60's Batman universe by focusing on silly capers and needlessly complex brainteasers. Very little is known about this version of the Riddler's backstory, the series paints him as a mystery from birth. The character, like in many other iterations, is compelled to leave behind clues, often to his detriment. He is fairly incapable physically, but his biggest weakness is his hubris and desire to prove himself. He regularly pulls off clever heists but leaves behind clues that the World's Greatest Detective follows straight back to him. This version of the character also appears in the film spinoff of the series as well as in the Legends of the Superheroes specials. The series created several mainstays of the character, like the question mark patterned business suit and question mark cane.

Batman Forever (1995)

The Riddler as depicted in Batman Forever

Almost 30 years later, the Riddler returned to the big screen in Joel Schumacher's 1995 film Batman Forever. This is, or was, likely the most iconic on-screen version of the character, brought to life by the incredible Jim Carrey. This is the first live-action version of the character to say his real name. This version of Edward Nygma is an inventor who works for Bruce Wayne, crafting dangerously amoral devices that Wayne is immediately suspicious of. Nygma discovers that an invention of his is capable of stealing the mental acuity of others for his benefit and immediately begins a reign of terror.

RELATED: Paul Dano Vs Jim Carrey: Who Is The Better Riddler?

Nygma begins sending threatening riddles to his now-former boss and stealing immense sums of wealth alongside fellow villain Two-Face. Riddler deduces that Wayne is Batman, then kidnaps his sidekick Robin and his girlfriend. Batman defeats the Riddler, but in doing so, causes him serious brain damage, leaving him in Arkham for good. This version of the character is darker, but still remarkably silly. Carrey was and is a comedic actor, so his turn as the Riddler is more about dancing and punchlines than any actual menace, even as he does some terrible things.

Gotham (2014-2019)

The next live-action Riddler came from the long-running series Gotham. Nygma appears here as a forensic detective who works for Gotham P.D. and happens to speak in riddles. His role in the series takes on a number of interesting directions. More than any other iteration, this version is a sort of split personality, the Riddler is a villainous alter ego of Nygma. At times, the split personalities merge, turning Nygma from an awkward nerd into a cruel calculating villain, but they also often battle for control of the body.

Among the massive cast of villains in Gotham, Riddler is a bit more complicated. Consistently changing sides to fight former allies, whether it's attacking his former coworkers at the GCPD or attempting to murder the Penguin in vengeance. This was easily the most complex on-screen iteration of the character to date, but the newest adaptation unseats this precedent.

The Batman (2022)

The Batman Paul Dano as the Riddler

In Matt Reeves's new film The Batman, Paul Dano portrays the Riddler as a Zodiac Killer-style serial murderer who sends clues to the police. He certainly stands out as the grittiest take on this classic villain. Dano's take is also a rare case in which the character is granted some backstory. Here renamed Edward Nashton, as he is sometimes in the comics, this Riddler was born an orphan and had to grow up in terrible conditions. Whilst in Gotham Orphanage, Nashton was bullied for his love of puzzles and riddles. An early interaction with Bruce Wayne led him to an entrenched hatred of the presumed elite and all those with money. Nashton holds an intense superiority complex that leads him to try proving himself over all others.

As a teen, Nashton attempted to murder a group of young socialites during an illegal street race. He planted explosives on a rich man's car, but, to his chagrin, they survived. Nashton went years without another incident and even found a career in forensics like his Gotham counterpart. He threw all that away, however, after burning his old orphanage to the ground in rage. Nashton discovered that he felt nothing after this act of vengeance, and searched desperately to discover his new purpose. Turning back to his childhood love of puzzles, Nashton started leaving behind cryptic clues to his misdeeds. Shortly thereafter, he donned a baggy green suit and set to work committing various high crimes for the following two years.

Nashton's plan within the plot of The Batman is focused on rooting out corruption in Gotham, largely by torturing and murdering the morally questionable elite. He develops the classic perceived rivalry with Batman over the course of his crime spree, leaving clues at each crime scene to lead Wayne in the right direction. He kills the mayor, targets organized crime leaders, and sends a bomb into the mayor's funeral. He's portrayed as both a domestic terrorist and serial murderer. He's simultaneously the least threatening Riddler physically, and the most intimidating and outputting. Dano's performance feels less like a comic book supervillain and much more like a biopic of a serial killer. He's a fun villain, for as grim and unsettling he is, and without wishing to spoil, the ending leaves the possibility that he could come back someday.

With these four live-action depictions, it's shocking to see how much can spring forth from an idea as simple as a man who leaves puzzling clues to his own crimes. From a question mark patterned leotard to an unhinged serial murderer, the Riddler has range.

MORE: What Villains Should Be Expected In The Batman Sequel