DC's The Riddler has captured the minds of audiences ever since his debut in Detective Comics #140 (1948) and is among the "big four" villains of the classic Batman rogues gallery. In nearly every incarnation, the complex puzzles and riddles he poses are a game that only he appears to be enjoying.
The extent of his obsession with puzzles may vary, as well as his hubris, but one thing's for sure. The Riddler is one of the few rogues who have made the Batman question his status as "the world's greatest detective."'
The Brave and The Bold (2008)
The Brave and The Bold offers a classic interpretation of the character, a clever trickster who is prone to overly complex plans and executing them with childish glee.
This Riddler (played by John Michael Higgins) is the perfect foundation of what a Riddler character should be, and the fact that he manages to remain menacing in a Scooby-Doo Movie is hilariously impressive.
Assault on Arkham (2014)
Assault on Arkham is among the best of the Suicide Squad's on-screen appearances. The Riddler is their current target in this movie. Voiced by Matthew Gray Gubler of Criminal Minds fame, Matthew channels a mean version of Spencer Reid for this role.
Riddler openly challenges Amanda Waller to a match of wits, unaware that she plays incredibly dirty. However, that doesn't stop Riddler's stride and he continues to smugly throw in Waller's face how he found the information she so desperately wants.
The Batman (2004)
If Brave and the Bold's Riddler was as classic as it gets, this goes in a completely different direction, design-wise. This Riddler, played by Robert Englund AKA Freddy Kruger, looks like the Batman Forever version of Marilyn Manson. However, that's not to say his character isn't fantastic.
This Riddler is one of the most sympathetic portrayals yet, a man who was abused by his loved ones, and only resorted to crime after all the bitterness he endured. His honest conversation with The Batman about his past shows a Riddler who truly wished it had gone any other way.
Harley Quinn (2019)
Gotham's "funniest villain," much to Joker's frustration, this version of the Riddler is indeed a hilarious version of the character. Voiced by Jim Rash of Community fame, this Riddler is a deadpan snarker who knows his own hype. His casual and unlikely"friendships" with villains and heroes alike is fun to see.
In many ways, this Riddler is probably the most socially capable of any hero on this list, barring perhaps the '60s version. His pragmatic approach to villainy is also a relatively new addition to his character, and his riddles are more a fun hobby than a compulsive obsession.
DCAU (1992)
The Riddler in the DCAU is similar to his The Batman (2004) version, a disgraced genius who seeks revenge on the companies that wronged them. Only this time, gone is the angst, and instead, audiences get the campy and smug scheming that Riddler is famous for.
The Riddler revels in his own intelligence and wants nothing more than to trade barbs with the caped crusader while he watches from a distance. His smugness is off the charts and seeing him get his just desserts eventually was gratifying. Though it has to be said, it took two episodes before Batman finally beat him fair and square.
The Batman (2022)
As far as Riddlers go, this is the most unorthodox take on the character yet. Gone are the iconic suits and fancy hats, this Riddler is a lot grittier and unsettling. His thick clothing, mask, and brutal methods evoke the spirit of the Zodiac Killer in the movie Zodiac, a disturbingly real threat that audiences immediately recognize.
There are even hints of Saw as seen with the elaborate death traps he subjects his victims to in the movie. This Riddler is completely unhinged yet dangerously elusive and intelligent. Without a doubt, this is the most menacing version of the character to date.
Batman (1966)
Leaving the realm of gritty realism now is the time for some 1960s absurdity with Frank Gorshin's Riddler. The Riddler is the first foe that Batman ever faces in live-action, and it's a heck of a debut into the mainstream. Frank Gorshin set the mold for the character's foreseeable future, making it one of the best Batman villain portrayals ever.
Switching from manic laughter to smug intelligence at the drop of a hat, The Riddler of the 1960s Batman show easily rivals the Joker for the title of Adam West Batman's most iconic foe. Fun fact, Frank Gorshin was so good in the role he won an Emmy for it, making him the first actor ever to receive one for playing a comic book character.
Gotham (2014)
Paul Dano portrayed the deranged. gritty yet methodical side of the Riddler character, while Gorshin reveled in the inherent campiness of playing a guy in a green suit asking complex puzzles. Cory Michael Smith's portrayal of Edward Nygma as a major villain in Gotham combines the best of both worlds masterfully. Smith's mixture of the smug trickster and terrifying serial killer is incredible.
Like Gorshin, Smith's Riddler has a penchant for dapper suits, over-the-top schemes that are both threatening and absurd. Like Dano however, he's socially awkward, and his bitterness towards society drives him to become a ruthless murderer. Add the manic mood shifts of both, and few can say that Smith isn't a fantastic portrayal of The Riddler.