Spoilers for The Batman, now streaming on HBOMax.
Today, we learn when Riddler first used his iconic catchphrase, "Riddle me this" in the comics.
In "When We First Met", we spotlight the various characters, phrases, objects or events that eventually became notable parts of comic lore, like the first time someone said, "Avengers Assemble!" or the first appearance of Batman's giant penny or the first appearance of Alfred Pennyworth or the first time Spider-Man's face was shown half-Spidey/half-Peter. Stuff like that.
In the recent hit film, The Batman, director Matt Reeves played with people's expectations by having the Riddler be the main villain in the movie and yet have the villain never actually use the phrase, "Riddle me this" in the film, but instead, a character who is almost certainly the Joker is the one who says it to the Riddler when the villain ends up in Arkham Asylum at the close of the movie. The almost-certainly-the-Joker says, "Riddle me this, the less of them you have, the more one is worth" and then reveals that the answer is "a friend."
HOW DID THE RIDDLER ORIGINALLY POSE HIS RIDDLES TO BATMAN?
The Riddler made his debut in 1948's Detective Comics #140 (by Bill Finger, Dick Sprang and Charles Paris)...
The interesting thing about the character is that, in his first appearance, there really weren't very many actual RIDDLES in the story. The Riddler was more about being a general puzzle guy, ya know? For instance, the Riddler introduces himself to Batman by first forcing him to fill out a giant crossword puzzle. Then he forces him to fill out a giant jigsaw puzzle. Next, he makes him figure out a chain puzzle before the rich guy that the Riddler just robbed is suffocated by the riddle. As I noted in a recent When We First Met, while the Riddler didn't actually KILL anyone in the comics for many years (not until the late 1970s), he certainly didn't seem to be too concerned about ALMOST killing people. And in fact, that was how the Riddler first actually posed a riddle to Batman and Robin, by pasting the riddle on to the side of a driverless truck that he let loose on Gotham's city streets, unconcerned if it killed anyone...
The oddest thing about the Riddler is that he appears to die at the end of his first appearance, but it's clearly intended to set up his next appearance, which came two issues later. Therefore, Bill Finger knew he would be bringing Riddler back as soon as he wrote the first story, which is a significant piece of confidence in the character, but then he just didn't use him again for over a decade!!! That's so weird.
In that second appearance, just two issues later, the Riddler actually DID so riddles this time, but he cleverly did very public riddles as part of a contest designed to get a whole lot of people at a place at a certain time to distract from his crimes at those same places. His riddles were done written down, though...
Later, he gives Batman a riddle verbally for the first time, and it's just "Here's a riddle for you"...
The Riddler then vanished for almost TWENTY YEARS before Julius Schwartz took over as the editor on the Batman books in the 1960s and he brought one of his star writers, Gardner Fox, with him, and I guess Fox looked through back issues for ideas and found the Riddler, bringing him back in 1965's Batman #171 (by Fox, Sheldon Moldoff and Joe Giella)...
The issue famously was one of the comic books that William Dozier read while developing the Batman TV series, which is why it was adapted for the first episode of the Batman TV series in 1966.
In the issue, though, the Riddler actually delivers his riddles to Batman by writing them down on pieces of paper...
It's worth noting that one of the riddles was about four guys on a boat with no matches, so how could they smoke? By throwing one of the cigarettes off of the boat, they became a cigarette lighter...
Eight issues later, in a story by Fox, Moldoff and Giella, the Riddler gives another written riddle...
He then intentionally DOESN'T give Batman riddles, but then subconsciously continued to leave riddles for Batman, even though he disputes it at first, noting that he "cued no riddles"...
Interestingly, though, that issue took place AFTER the broadcast of the first Riddler episode of the Batman TV series! And as we see, the TV show is where the phrase made its debut.
WHEN DID RIDDLER FIRST SAY "RIDDLE ME THIS"?
As noted, the first episode of the Batman TV series was a fairly faithful adaptation of Batman #171, right down to using the "cigarette lighter" joke. However, on the TV series, Riddler leaves it for Batman and Robin as a RECORDING, and he opens by saying, "Riddle me this"...
So that's really the first time that the phrase was used by the Riddler, but if you want to look for specifically a time when he used the phrase in a COMIC BOOK, then you wouldn't have to wait very long, as later in 1966, in Brave and the Bold #68 (by Bob Haney, Mike Sekowsky and Mike Esposito), the issue is clearly written by Haney as a reference to the success of the Batman TV series and sure enough, Haney has Riddler using his now-famous catchphrase in the issue...
And the phrase has been a regular catchphrase for the Riddler in the comics ever since, although obviously it doesn't come up AS often as it does on the TV show (or as much as Jim Carrey used it in Batman Forever).
Thanks to longtime reader Nicole K. for the question! If anyone else wants to know about an interesting comic book first, just drop me a line at brianc@cbr.com!