The Riddler's Worst Moments In The Batman Ranked

The Riddler is one of the most iconic members of Batman's rogues gallery. Having made his debut in 1948's "Detective Comics" #140, the dastardly trickster has been plaguing the Dark Knight for more than 70 years, and continues to be a nuisance to this day. One of the things that sets him apart from other supervillains is his ability to be a threat without enhanced physical abilities like strength, flight, or laser vision. No, the Riddler's only weapon is his genius intellect, which he uses to create dangerous riddles, quizzes, and traps.

Over the years, the Riddler has been featured in numerous television projects, movies, and video games. 2022's "The Batman" brings him to life in a brutal new way, courtesy of actor Paul Dano, who gives the villain a sinister and grounded edge. This Riddler is a vicious monster who commits no end of atrocities: He terrorizes Gotham City with brutal murders, attempts to destroy Bruce Wayne's life, and builds an army of bloodthirsty followers. These are the Riddler's worst moments in "The Batman," ranked from the merely cruel to the enormously evil.

The Riddler begins as Edward Nashton, a former resident of an orphanage once run by Thomas and Martha Wayne, Bruce Wayne's parents. When Edward and Bruce were children, Thomas announced his run for mayor of Gotham City. But he and Martha were killed shortly afterward, leaving his promises of change unfulfilled.

In the final act of the film, the Riddler has been captured and incarcerated in Arkham State Hospital, but has left clues indicating he has one final act of mayhem planned. Batman interrogates him and learns that Edward has held a grudge against him since he was a child. When Thomas and Martha Wayne were murdered, the public's attention was focused entirely on young Bruce. This left the orphanage forgotten, whose terrible living conditions Edward describes to Batman in painful detail.

While Edward can't be entirely blamed for feeling jealous of someone who lived in a mansion while he suffered in a rundown orphanage, that's no excuse for taking things out on an entire city.

In a particularly brutal act, the Riddler leaks evidence to the public that Thomas Wayne hired crime boss Carmine Falcone to murder a journalist who threatened to publish information on Martha Wayne's history of mental illness. This is a massive emotional blow to Bruce, who's always believed his father was a spotlessly good person. He proceeds to confront Alfred about keeping this vital secret from him. 

While Alfred admits that Thomas hired Falcone to coerce the journalist into keeping Martha's history private, he also reveals that Thomas intended to turn Falcone over to the police when he heard about the murder. This is what provoked Falcone into arranging Thomas and Martha's assassination. Though the Riddler commits far more terrible acts in "The Batman" than this, his attempt to ruin an entire family's legacy stands out as uniquely cruel, and viscerally painful for Bruce.

As an imprisoned Riddler watches news coverage of Batman cleaning up his foiled plans, he weeps uncontrollably. However, he soon hears the voice of someone in the cell next to his — someone who seems sympathetic to his plight. "One day, you're on top; the next, you're a clown," the voice says. As the Riddler resumes sobbing, the voice consoles him by telling him how well he did, and assures him that "Gotham loves a comeback story." When the Riddler asks this person who they are, they reply with a question: "Riddle me this: The less of them you have, the more one is worth." "A friend," the Riddler answers. The voice begins laughing maniacally, followed by the Riddler's own malevolent cackle.

While fans have hotly debated who Barry Keoghan plays in "The Batman" (the actor is listed as playing "Unseen Arkham Prisoner" on IMDb), it's pretty safe to say he portrays the Joker. Befriending someone who commends you on your attempts to destroy a major city is always a bad idea, but when that person is the Joker — who is clearly cooking up larger plans –  it's safe to say you're about to make some really bad decisions.

As part of his plan to bring down Gotham City's elite and reveal their darkest secrets, the Riddler cultivates a large online following that is able to carry out his mission even in the event of his capture. He does this by releasing videos of himself committing crimes and declaring his vengeance on the corrupt rulers of the city.

This vengeance plays out in full when the Riddler is incarcerated in Arkham State Hospital. When he's interrogated by Batman, he reveals that he has placed car bombs throughout Gotham City. The bombs go off, destroying Gotham's breakwater walls, which causes considerable damage when the city is flooded. This upheaval is all part of the Riddler's scheme: The chaos acts as a distraction, enabling his cult-like followers to carry out the assassination of mayor-elect Bella Reál. However, with the help of Catwoman, Batman is able to take down the Riddler's "fans" and prevent the assassination from taking place.

It's not enough that the Riddler enacts a large number of heinous acts throughout the film — he also films them and releases the footage to "inspire" Gotham City's wayward minds. This elevates the Riddler from a common criminal into a genuine monster.

Batman and Lieutenant James Gordon investigate the ruins of the orphanage that was once run by Thomas and Martha Wayne. After examining the clues left behind by the Riddler, they discover his next victim is Bruce Wayne himself. Batman immediately rushes to Wayne Tower and tries to warn Alfred.

As Alfred is going through the mail at Wayne Tower, he opens a package addressed to Batman. Probably due to his time with British intelligence, Alfred swiftly realizes something is amiss and throws the package away, just before it explodes and causes considerable damage to Wayne Tower. Good thing Alfred is tougher than he looks: He survives, but is left seriously injured and is subsequently hospitalized. The Riddler's attack on someone so close to Batman proves just how much he knows about Batman's private life, and establishes how dangerous and ruthless he really is.

After Batman learns about his father's connections to crime boss Carmine Falcone, he and Gordon are lured by Catwoman, who reveals that Falcone strangled Annika, her roommate and possibly her girlfriend. She vows to kill Falcone herself, and takes off for the Iceberg Lounge with Batman and Gordon following closely behind.

Once there, Catwoman points a gun at Falcone and reveals that she is his daughter. But before she can fire a fatal shot, Batman stops her. He turns Falcone over to Gordon and the Gotham City Police Department. After he's read his Miranda Rights, Oswald Cobblepot pulls out a gun and prepares to kill Falcone himself. But then, Falcone is shot dead by the Riddler, who's ensconced in a nearby building.

Falcone is no angel, having committed plenty of crimes all over Gotham City over the course of decades. But the Riddler's murder is still completely unjustified — even if he is acting out of a warped sense of justice.

At the point of time "The Batman" takes place, James Gordon has not yet risen to the rank of police commissioner, the role he's most associated with. Instead, the commissioner of the Gotham City Police Department is Pete Savage. In stark contrast to Gordon's steadfast morality, Savage is deeply corrupt, having accepted bribes from various criminals.

Shortly after Mayor Don Mitchell Jr. is killed by the Riddler, Commissioner Savage holds a press conference. He announces the terrible news and promises to bring the Riddler to justice for his crime. However, before he can carry out this vow, he's killed by the Riddler. The villain leaves a message for Batman and releases a disturbing video of Savage's death to the public.

Savage is far from a decent person — he's even in Carmine Falcone's pocket. But murder is still murder, and slaying Savage stands as one of the Riddler's most sinister acts. Distributing footage of the killing makes this an especially cold-blooded crime.

District Attorney Gil Colson is another respected-yet-sleazy member of Gotham City's elite: Batman discovers early on that he's working for crime boss Carmine Falcone. However, this doesn't make his death at the Riddler's hands any less appalling.

During a funeral service for the late Mayor Don Mitchell Jr., a car careens into the church where everyone is gathered. Out comes Colson, who has a phone attached to his hand and a bomb attached to his neck. Bruce Wayne, who is attending the funeral, leaves, then returns as Batman to talk to the Riddler via the phone in Colson's hand. The Riddler threatens to set off the bomb unless Colson can correctly answer his three riddles. With Batman's help, Colson manages to answer the first two — but he can't bring himself to answer the third, which would necessitate revealing the informant who helped the Gotham City Police Department bring down crime boss Salvatore Maroni. The Riddler proceeds to detonate the bomb, killing Colson.

So, let's recap. The Riddler ruins the funeral service for the mayor he killed, kidnaps and torments the district attorney, and ultimately murders him. As if that's not bad enough, he also broadcasts the event live to his growing online audience. This is, without question, one of his most evil acts.

The Riddler's worst moment is also his first: Brutally killing the mayor of Gotham City, Don Mitchell Jr., on Halloween night. It's a brazen way to kick off his vicious campaign, and he couldn't have done it in a more cold-blooded way.

Shortly after watching news coverage of Mitchell's mayoral debate with Bella Reál, the Riddler sneaks into his home and viciously beats him to death. He leaves Mitchell's body propped up on a chair with his head wrapped in duct tape, with the words "NO MORE LIES" scrawled across his face. To add to the gruesomeness of this crime, Mitchell's thumb is removed and later found attached to a USB drive in his car, giving horrible new meaning to the phrase "thumb drive." It includes photos of Mitchell with another woman, Annika, confirming he was having an affair. Following this discovery, the photos are leaked to the media.

What makes this act the Riddler's worst moment is that it doesn't end with the mayor's murder. From cutting off his thumb to ruining his reputation after his death, this is all part of the Riddler's larger plan to reveal just how vile those who run Gotham City really are — according to the Riddler, anyway. While Mitchell is no saint, like so many of the Riddler's other victims, he's still a husband and father. Thanks to the Riddler's cruelty, his wife and child don't just lose him — they lose their unsoiled memories.