When it comes to Batman villains with the best sense of humor, the Joker is widely considered to be the funniest of the lot, thanks to his infamous gags and pranks. That doesn't mean fans should overlook the Riddler, though, whose ever-present riddles are often far funnier than anything the Joker cooks up. The Joker may be the Crown Prince of Crime, but the Riddler is the Prince of Puzzles, and his wordplay and wit are second to none. There have been numerous interpretations of Edward Nygma over the decades, and exactly how funny he is depends on the tone of each distinct version, but even the character's darker reimaginings are capable of unleashing a rib-tickling riddle or two.
As the two most common modes for the Riddler are "merry trickster" or "sociopathic mastermind," his funniest riddles tend to be either a classic dad joke that earns a reluctant chuckle or something that may get a shocked giggle out of those who prefer their jokes as dark as Batman's cape. Sifting through 80 years of riddles from across movies, TV, games, and comics, there are plenty of comical conundrums to choose from, but these are some of the very best.
12 "What Is It That No Man Wants to Have Yet No Man Wants to Lose?"
Answer: "A Lawsuit!"
The camp classic that is the 1960s Batman show started as it meant to go on with its first-ever episode, "Hi Diddle Riddle," which introduced the world to Frank Gorshin's iconic incarnation of the Riddler. With the writers' well of puns and wordplay not having yet run dry, the Riddler's riddles in this opening installment aren't as absurdist and surreal as they would become.
Instead, the Riddler's riddles are a little sharper and smarter. Like, for instance, this snappy retort to Batman attempting to arrest him, which sounds like a joke passed around at a law office's Christmas party.
11 "What Are the Chilliest 12 Inches in the World?"
Answer: "Cold Feet."
In Batman Season 3, Episode 2, the Riddler develops a previously-unseen interest in prize fighting. At this point of the show, it certainly seemed like the writers were having trouble thinking up any more villain plots.
Thankfully, the newfound sports fan doesn't ditch his riddling shtick and delivers this chucklesome dad joke to Batman over the phone, while attempting to goad the Caped Crusader into agreeing to a bare-knuckle brawl at Gotham Garden. This ended up being Riddler's final appearance on the Batman show, so viewers are left to presume that he must have quit the crime business and become a pro-fighter.
10 "How Can One Get Into a Locked Cemetery at Night?"
Answer: "A Skeleton Key."
In Batman #179, Batman and Robin are called in when the Riddler somehow breaks free from his jail cell and leaves a clue as to how he did it scrawled on the wall. "To know how I escaped, solve this riddle," the Riddler's message reads, followed by the playful yet gothic query above.
Batman quickly deduces the answer and speculates that the Riddler created his own skeleton key while in the prison workshop. So fans can apparently add master locksmith to Nygma's ever-growing list of skills.
9 "How Do You Make a Dishonest Shortcake?"
Answer: "A LIE-berry Shortcake."
By the end of Batman's first season, coming up with nifty new riddles was clearly taking its toll on the writers, hence this gloriously convoluted puzzle from Episode 31, "Death in Slow Motion." On the Riddler's tail after he initiates a bizarre crime spree across Gotham, the Dynamic Duo arrive at a bakery to find a riddle written on the wall.
Somehow, not only does Robin follow Riddler's twisted logic to come up with the nonsensical answer, but Batman then realizes that "lie-berry" is "clearly a corrupted version of the word 'library'" and infers that is where the Riddler is hitting next. And that is exactly why Batman is the World's Greatest Detective.
8 "Why Is Corn Hard to Escape From?"
Answer: "Because It's A Maize!"
History was made in 1948's Detective Comics #140 when Batman and Robin faced the Riddler for the very first time in print. From his familiar costume and color scheme to his penchant for spoiling his own schemes by leaving handy clues at the scene of the crime, all the iconic elements of the Riddler were present from his very first appearance.
The Riddler's first ever riddle was one for the ages, a self-sabotaging teaser that led Batman to deduce he was lying low in an amusement park maze. In a life of crime filled with corny puns, this is for sure the corniest.
7 "Who’s Sweaty, Scared, and Expandable?"
Answer: "You!"
The Riddler isn't traditionally viewed as one of Batman's most sinister foes, generally due to the lingering influence of the '60s version, but occasionally the comics have dialed his dark sense of humor all the way up. In 1990's Batman #452, the Riddler takes two security guards hostage, leaving one of them terrified for his life.
"Who's sweating, scared, and expendable?" the Riddler quips, before answering his own riddle. "You," he says, before shooting the poor security guard in the head. Frank Gorshin would never.
6 "What's Green, Sits in the Bathtub, and Whistles?"
Answer: "A Salami."
In 1988's Secret Origins Special, a TV news crew attempts to get Edward Nygma to open up about his childhood, but all he tells them is a supposed anecdote from his youth about the time his father tested him with a particularly perplexing riddle. When his father revealed the bizarre answer to the above riddle, little Eddie had questions. "But a salami isn't green?" he asked, to which his dad replied, "You can paint it green."
Eddie then countered, "A salami doesn't sit in a bathtub!" His father responded, "You can put it in a bathtub." The young Eddie thought he'd gotten the last word when he declared, "But a salami doesn't whistle!" His dad's explanation? "Ahhh, I just put that in there to make it difficult."
5 "How Does an Exhibitionist Garbage Collector Break Up With His Girlfriend?"
Answer: "He Dumps Her in Public."
1995's Batman: Riddler and the Riddle Factory special may have been released to tie in to Batman Forever, but its depiction of the Prince of Puzzles is much darker than Jim Carrey's incarnation. In this comic, Riddler has become a cult media figure thanks to his underground TV game show in which "volunteers" from the audience have to answer his riddles correctly or else face a gruesome punishment.
Luckily for them, the contestant faced with this riddle guesses the punny punchline correctly, narrowly avoiding the business end of Riddler's rapier and getting taken out with the trash.
4 "What Animal Walks on Four Legs, Two Legs, and Three Legs?"
Answer: "A Baby."
The above riddle, also known as the Riddle of the Sphinx, has got to be the most famous riddle in the world, and the Riddler put his own blackly comic — think jet-black — twist on it in Batman: Arkham Asylum. When he poses the question to his therapist, she naturally assumes the answer is "a human being," as per the old myth: a baby crawls on four limbs, an adult walks on two, and the elderly use a cane to make three.
How can the answer be just a baby? The Riddler says you could cut off its arms and then give it a crutch. "That's horrible," retorts the disturbed therapist. "How can you even joke about something like this?" The Riddler shrugs and replies, "Easy, it's not my baby."
3 "I Could Lend You a Hand, but You Won’t Find Me Helpful. My Name May Sound Tasty, but the Flavor Is Dreadful. What Am I?"
Answer: "A Knuckle Sandwich!"
As Gotham diehards know, Cory Michael Smith's portrayal of Edward Nygma is one of the most underrated takes on the Riddler across all Bat-media. He had to tussle for screentime among all the other proto-supervillains in the prequel show's ensemble, but every now and again, he would come out with an instant classic of a riddle that rivaled the character's best.
Case in point, this cleverly worded question from Gotham Season 4, Episode 15. In this case, the victim is none other than Oswald Cobblepot, who is subsequently knocked out by a guard on Nygma's payroll.