The Riddler has been a worthy adversary to Batman’s mind since Detective Comics issue #140 in 1948. He’s filled with brain teasers, puzzles, traps, and an ego the size of Gotham City itself. The character has been an established villain in DC Comics for well over 70 years, so it was bound to happen that The Riddler would commit some heroic acts.
The frequent enemy of Batman has undergone a few changes, both mentally and physically. His outfits have ranged from green leotards to snazzy suits, and in The Batman, to a military ski mask. His mental changes have also been quite the trip, and his heroic endeavors are wild.
8 Kept Batman’s Identity A Secret
From Jeph Loeb, Jim Lee, and Scott Williams comes Batman: Hush. Riddler plays quite the role in this graphic novel, and he confirms to Batman he was dying of a brain tumor. As it turns out, The Riddler used The Lazarus Pit without Ra’s al-Ghul’s permission to cure himself.
Instead of being driven insane by the pit, he was invigorated with clarity that Bruce Wayne is Batman. It may not be entirely heroic, but Riddler kept this secret to himself. Not out of heroism for Batman, but because then everyone would know, and thus his biggest riddle would be worthless.
7 Tracking Down Clayface With Mary Marvel
Countdown issue #42 has the famed Mary Marvel patrolling the Gotham City streets until she stumbles upon the ever recognizable, green suit-wearing Riddler. She scoops him up into the air, but Riddler protests that he is reformed, and as such, Mary Marvel reluctantly takes him with her to follow a muddy trail.
This trail leads the duo to Clayface, where Mary Marvel makes short work of the monster with her newfound powers. It’s a nice moment between Mary Marvel and Riddler, where he tells her she should seek a mentor for her anger issues.
6 E. Nigma, Consulting Detective
The character Shining Knight hit The Riddler in the skull with his mace and gave Riddler quite the brain injury in Infinite Crisis issue #7. The result of this injury wasn’t seen until a year later in Detective Comics issue #822, but Riddler appears, and it is entirely reformed as a consulting detective.
Riddler’s newfound love of detective work makes his brilliance in solving crimes a fun one. His loud, egotistical personality shines through as a detective, as he seeks to prove to everyone, including the media, just how great he is, and how he will solve Gotham's true villain: itself.
5 Saving Batman With A Flaming Arrow
Issue #828 of Detective Comics sees one of Bruce Wayne’s oldest friends dead in Gotham Bay. The man was ripped apart by sea monsters. A bizarre death, so close to home, Batman investigates, with Riddler one step ahead due to his talents as a private detective.
Batman is ambushed, and hangs off a building’s gargoyle statue, with a villain ready to stab him and make him plummet to his death. Luckily, Riddler is there. He leaves behind the great riddles and with a flaming arrow from a bow, he shoots the villain and watches him burn whilst taunting him. Batman puts out the fire, and it shows a moment where Riddler could have easily let his former adversary die.
4 Riddler’s War On Drugs
A reformed and investigative Riddler embarks on a mission from none other than Bruce Wayne in issue #837 of Detective Comics. Not only does Riddler feature in a heroic moment, but it is assisted by none other than the other reformed Gotham Rogue, Harley Quinn.
Riddler seeks Harley’s help in the search of a woman named Lisa Newman, who Riddler suspects of stealing new regenerative drugs from Wayne Industries.
3 Helping Batman End The War Of Jokes And Riddles
In Tom King’s 2016 run of Batman, one arc, in particular, puts Joker and Riddler in the center of Gotham’s latest carnage. The War of Jokes and Riddles has The Riddler and The Joker in a long and bloody war in the deciding factor of who gets to kill Batman. Their feud starts after Joker shoots Riddler, just to see if it would make him laugh.
After inviting them both to dinner, Bruce Wayne decides to judge which side is worse, meaning that the easier side to take down must win. Batman assists Riddler, and together, they take down Joker and his villainous forces. Although, Batman does apprehend Riddler and his crew immediately afterward.
2 Deducing The Conundrum
In Gotham City Sirens issue #3, Riddler takes the centre stage as the private detective. After consulting with Batman, he is informed of a string of faux suicides. The latest victim is a woman called Alison Gulbraith, and Batman tasks The Riddler with looking after her twin sister, Angela.
Riddler saves the girl from an explosion, and while he is at it, manages to deduce the identity of those responsible for these fake suicides. He boasts to Conundrum her name and occupation, all a distraction as he waits for Batman to arrive on the scene.
1 Saving Nightwing
In Gotham Underground, Riddler commits his most heroic act yet. He saves Nightwing’s life. The act of saving his former adversary’s ward is a noble one. Riddler dragged Nightwing out of the alley where he was bleeding and dying and brought him to a medical clinic that saved his life.
Not only did Riddler save Nightwing, but he also figured out his disguise as Freddie Dinardo. This, of course, was a fake identity that Nightwing had used, but Riddler deduced it nonetheless. He also made Nightwing aware of the fact, that his secret is still safe since he can’t put a name to his face. This is a big secret many villains of Gotham and Blüdhaven would adore, yet it’s Riddler’s one to keep.