Within The Dark Knight's gallery of memorable and iconic villains, the Riddler stands out alongside The Joker as an icon. When fans see a green question mark, they can instantly recall some of their favorite stories, episodes, and movies.
Over the years, the Riddler became a symbol of mystery and intrigue alongside crime in DC. As the stakes grew higher, so did the depth of riddles. Every riddle left behind ranged from simple to esoteric, and when coupled with a crime, these riddles took on a life of their own. Intent adds weight, and that weight is hidden behind a question. That hidden weight, only revealed by failure or success, leaves many readers thinking about the riddles far after the story ends.
10 Batgirl Runs The Riddler's Gauntlet
The Riddler has matched wits with Batman many times. He isn't limited to Batman though. There are times when the Riddler has challenged other members of the Bat-Family. Batman Confidential #21, written by Fabian Nicieza with art by Kevin Maguire and I.L.L, pits Batgirl against the Riddler to get her father's case journal.
To retrieve her father's journal, Batgirl must travel through the Riddler's gauntlet of riddles in Arkham. One of the most challenging riddles is a face-off against the Joker. Despite his cruel demeanor, the Joker is actually very smart, so this battle of the wits is very dangerous.
9 A Riddle For Robin's Missing Partner
Batman Gotham Adventures is the follow-up to the award-winning Batman animated series. Issue #57, written by Scott Peterson with art by Tim Levins, Terry Beatty, and Lee Loughridge, follows Robin as he attempts to find Batman. With the aid of Kim, a Riddler copycat, the two decipher the riddles to find Batman's location. The hardest is the last.
The final riddle is a collection of words and an image. It stumps Robin and Kim with its oddly simple structure. Alone, they are just a collection of scientific terms. The answer lies in the definitions of the words, which elevates this riddle.
8 A Riddle For The Masses
As DC's Rebirth entered its full swing, Detective Comics #1059, written by Mariko Tamaki with art by Brad Anderson, Danny Miki, and Ivan Reis, saw the return of the Riddler as a threat to Gotham. This time. he returned to the city as a daily streamer, speaking with a populist message alongside a series of crimes.
The true value of this riddle is its misdirection. Normally, the Riddler signals his crimes with a riddle, but this was actually about a person. The answer directly refers to a court judge and her past misdeeds. Because of this misdirection, Batman was outsmarted and unable to tie the Riddler to the crimes.
7 A Riddle For A Long Night
In Batman: Year Zero, written by the critically acclaimed Scott Snyder with art by the award-winning Greg Capullo, the Riddler shuts down all power in the city before a storm hits. The storyline features the most turmoil in the city before Joker War.
The Riddler asked the people of Gotham, "There are two sisters; each gives birth to the other. Who are they?" The answer is Night and Day, but there is a deeper layer. The Riddler is working with Doctor Death on this attack. Their separate plans feed into one another as the city descends into chaos. This secondary meaning is masked by the power outage and the focus on night.
6 The Riddle For A Team-up With Batman
Batman: Run Riddle Run, with art and story by Mark Badger and Gerard Jones, features the return of Riddler as a security consultant for Ms. Diforza, using his intellect and criminal past to help boost her company's standing in Gotham. This leads to a cascading series of events that land the Riddler and Batman on the same side to stop a threat to Gotham.
Regarding teaming up, the Riddler hid for Batman to find him later. Despite his compulsion for riddles, this riddle actually wasn't a hint about a crime. In this riddle is Edward's location for Batman to find him because he is being hunted by the same people who framed Batman.
5 Will The Real Riddler Please Stand Up
When Edward Nigma became the Riddler and began his criminal career, he saw himself above the basic Gotham thug. He views his riddles, and by extension crimes, as an art form. When ClueMaster, Arthur Brown, began using the Riddler's shtick it was only a matter of time before they clashed. Riddler had to clarify who was the real master of conundrums.
Detective Comics # 706, written by Chuck Dixon with art by Greg Nolan, David Roach, and Gloria Vasquez has Batman and Robin save ClueMaster's life after the Riddler attached a bomb to him. The bomb and city-wide game of clues are all a distraction, though. The Riddler, Echo, and Query are out to steal baseball history. The first line of "Old Testament" hints at the baseball game and the numbers match the innings and the game date. This riddle proves Edward is smarter than Arthur, but also able to outsmart Batman by having him run around Gotham.
4 When Is A Riddle Not A Riddle
Many readers often overlook the Silver-Age crimes of the Riddler as an era marked by immature antics. However, one of the Riddler's most interesting and complex riddles is within that era. Batman #171, written by Gardner Fox with art by Sheldon Moldoff and Joe Giella, sees the Caped Crusader and Boy Wonder confounded by the Riddler.
In Remarkable Ruse Of The Riddler, the Riddler, recently released from prison, returns to his usual criminal ways. He doesn't leave his usual style of clues though. The Riddler frames himself as committing crimes while Batman and Robin observe and fools them with his innocence when they act. The Riddler's innocent actions are actually clues to the true crime he plans on committing: robbing The Gotham Times' anniversary party.
3 Blowing Up On The Art Scene with Riddles
The Riddler was introduced into the Batman mythos in Vol. 2 of Batman: Earth-One. Earth-One, written by Geoff Johns with art by Brad Anderson and Gary Frank, reimagined The Dark Knight of Gotham alongside the Riddler. The Batman film from 2022 could be inspired by this interpretation. Their methods are the same, and the riddles are just as deadly.
The Riddler introduced himself to Gotham and Batman with a riddle staged at an art showcase. The riddle is simple and relies heavily on environmental context. It becomes one of the better riddles when the failure to solve it results in an explosion. It embodies the simplistic yet dangerous nature of the riddles.
2 The Riddle Of The Sex Offender
The Riddle Factory, written by Matt Wagner with art by Dave Taylor and Linda Medley, features the Riddler on the hunt for a hidden cache of money in Gotham. In usual Riddler fashion, he makes a show out of the hunt with a literal pirate television show.
The pirate television show that the Riddler runs features one riddle that contestants slowly solve. These riddles are more than entertainment. They are huge exposés of the Gotham elite. The Dirtiest is the artist who assaulted girls. The Riddler uses this riddle to draw attention away from his crime and to the hidden crimes of the wealthy.
1 The Day The Riddler Came To Star City
In a Pre-Flashpoint run of Green Arrow, written by Judd winick and featuring art by Phil Hester, Ande Parks, and Guy Major, the Riddler took Star City by Storm with a crime spree. Using the Star Sentinel as his personal billboard, he signaled his crimes. This method and the unorthodox crimes, such as tying an elephant to a balloon, kept Green Arrow on his back foot as he grappled with Dinah leaving.
The threat escalated drastically when the Riddler painted the riddle. The riddle uses syllables, rhymes, and a historical reference. When read aloud, it sounds disjointed. When Green Arrow breaks it down, it gives the location of the bomb and the type of bomb. It is a cleverly structured threat.