8 Worst Things The Riddler Has Ever Done

Riddle me this: What’s purple and green, and bleeds profusely?

The Riddler Hush
DC Comics

Having made his comic book bow in 1948's Detective Comics #140, The Riddler has gone on to be one of Batman's most beloved and infamous rogues. Of all the names to have tangled with the Caped Crusader over the decades, few are as notable or have done as much damage as Edward Nygma.

Whether it's from his time in the funny books, his various live-action appearances, video games, or even animated outings, Nygma has proven to be one of the Dark Knight's most challenging foes. He may not be a brutal bruiser or beefed-up tough guy, but Eddie has something that few other villains have - an IQ that's more than enough to push Batman to his absolute limit.

Like all good villains, The Riddler has done some truly devious, shocking things during his career of criminal activity. And there's an argument to suggest that Nygma's antics are even worse than his villainous colleagues due to the fact that he often targets the mind and mental toughness of the World's Greatest Detective.

On that trail of thought, then, here are the eight worst things that Edward Nygma has ever done...

8. Drugging Barbara Gordon

The Riddler Hush
DC Comics

DC Comics’ Elseworlds stories always allow for things to be shook up a little, and the alt-world Thrillkiller tale saw The Riddler become a total creep. Well, an even bigger creep than usual, that is.

Thrillkiller takes place in a 1960s Gotham City in which Batman doesn’t exist. While the Caped Crusader is absent from this world, Gotham does still have a Batgirl and Robin. And it’s with Barbara Gordon that Edward Nygma’s eerie side really starts to show itself.

In this ‘what if?’ story, Nygma is a psychiatrist and award-winning author rather than an all-out, suited ‘n’ booted supervillain. That doesn’t mean he’s not a nasty piece of work, however. So much so, Edward takes advantage of Barbara upon her deciding to pay him a visit in a patient capacity.

Purposely giving her ridiculously strong Valium and other medication, Nygma turns Batgirl into a near-comatose zombie who hangs around people she’d never usually associate with. And it’s not even Barbara who manages to put a stop to all of this, for Riddler’s sinister game is only halted once Jim Gordon and Alfred step up and strongarm the villain.

Senior Writer
Senior Writer

Once described as the Swiss Army Knife of WhatCulture, Andrew can usually be found writing, editing, or presenting on a wide range of topics. As a lifelong wrestling fan, horror obsessive, and comic book nerd, he's been covering those topics professionally as far back as 2010. In addition to his current WhatCulture role of Senior Content Producer, Andrew previously spent nearly a decade as Online Editor and Lead Writer for the world's longest-running genre publication, Starburst Magazine, and his work has also been featured on BBC, TechRadar, Tom's Guide, WhatToWatch, Sportkskeeda, and various other outlets, in addition to being a Rotten Tomatoes-approved film critic. Between his main dayjob, his role as the lead panel host of Wales Comic Con, and his gig as a pre-match host for Wrexham AFC games, Andrew has also carried out a hugely varied amount of interviews, from the likes of Robert Englund, Kane Hodder, Adrienne Barbeau, Rob Zombie, Katharine Isabelle, Leigh Whannell, Bruce Campbell, and Tony Todd, to Kevin Smith, Ron Perlman, Elijah Wood, Giancarlo Esposito, Simon Pegg, Charlie Cox, the Russo Brothers, and Brian Blessed, to Kevin Conroy, Paul Dini, Tara Strong, Will Friedle, Burt Ward, Andrea Romano, Frank Miller, and Rob Liefeld, to Bret Hart, Sting, Mick Foley, Ricky Starks, Jamie Hayer, Britt Baker, Eric Bischoff, and William Regal, to Mickey Thomas, Joey Jones, Phil Parkinson, Brian Flynn, Denis Smith, Gary Bennett, Karl Connolly, and Bryan Robson - and that's just the tip of an ever-expanding iceberg.