There were but two Riddler stories published during the Golden Age,* the first being...
DETECTIVE COMICS #140 - "The Riddler"
The Riddler has a fairly nondescipt origin story: basically he was a kid who cheated at puzzles. When he grew up, he got himself a costume and decided to pit himself against the law. For his first public appearance, he took over a changable electronic billboard which displayed different crossword puzzles and clues. He tied up the operator with a Houdinin rope tie and put up the following puzzle:
- 1 Across - A water utensil (five letters)
- 1 Down - A formal dinner (seven letters)
- 2 Down - A public way (six letters)
I'll pause while you figure it out.
Back? Okay. Batman figures "a five-letter word for water utensil" is "basin"; Robin contributes that "a six-letter word for "a public way" (beginning with "S") is "street"; finally, Batman concludes that "a seven-letter word for "a formal dinner" is "banquet." Put them all together and they indicate "Basin Street Banguet" which is a charity event being held at the Basin Street Hotel that night. No sooner do they arrive, though, than word arrives that a water main has burst, flooding the bank nearby. "A bank flooded?" realizes Batman. "A bank-wet! That's what the Riddler really meant! He tricked us neatly!" By the time they get there, the riddler is already on the scene, wearing a diver's helmet and robbing the flooded underground vault. He escapes through the sewer.
The Riddler's next clue is a giant puzzle, so big it must be assembled in the Gotham Football Stadium, with Batman directing the operation from above over the stadium's P.A. sustem. The puzzle reads: "Tonight I shall rob the eagle's nest." Robin figures and "eagle's nest" is an eyrie," and Batman contributes that "there's an Eyrie Nightclub atop a downtown skyscaper." But again the Riddler has cheated. Actually he is robbing the home of Harrison Eagle, the millionaire collector. Batman and robin have split their forces this time, however, Robin taking the nightclub and Batman taking the millionaire's mansion. The Riddler tosses a smoke bomb along with the bon mot "where was Batman when the lights went out?"** Batman cannot pursue him, however, because he has left Eagle in a constricting puzzle threatening his life.
Giant prop: Riddler next crime involves a huge cob of corn stolen from the Higgens Canned Corn company: "Dear Batman: Here's a corny riddle to tip off my next job. Why is corn hard to escape from?" Brainstorming together, B&R figure out that "maize" is another name for corn, and that there's a big glass fun maze at Pleasure Pier Amusement Park. By the time they get there, Riddler has already stolen the receipts by using a cane to trip up the guard "by means of an acrostic" (a-cross-stick, which is more of a pun than a riddle). B&R pursue him into the maze, but again the Riddler cheats, by sealing off the maze's one entrance/exit. What's more, he has set a bomb to explode in 30 minutes (which hardly seems sporting). B&R escape the maze by lighting the carpet on fire, which causes the metal frame to expand just enough to pop the glass pane out.
B&R run to safety, but the Riddler is caught in the blast. He is blown into the harbor where the only sign of him is the question mark from his costume rising to the surface. did is come off when he drowned? Or did he leave it behind as a puxxle? "Only time will solve that riddle!" say the Batman
*This one can be found in reprinted in the Batman From the '30s to the '70s HC and the Batman: The TV Stories tpb.
**In the dark.

Replies
DARK KNIGHT, DARK CITY:
Batman #452-454 is a bi-weekly fill-in by Peter Milligan and Kieron Dwyer, and the first Riddler story to be published after the wonderful "When Is a Door" from Secret Origins Special #1. Not surprisingly, the new "Secret Origin of the Riddler" was ignored in favor of this "grim 'n' gritty" revision. It involves black magic, demonism and human sacrifice. Step-by-step, the Riddler manipulates the Batman through the ritual to prepare himself for human sacrifice. He must 1) Kiss the lips of a hanged man, 2) Bathe in human blood, 3) Participate in a "danse macabre" with the dead, 4) Slay a wild dog with a silver dagger, 5) Slit the throat of an unbaptized child, and 6) Dance in a black sabbath mass. And no, it doesn't help that the riddler was posessed by the demon Barbathos all along.
Batman didn't even realize he was performing steps in a Satanic ritual. For example, when he "slit the throat of an unbaptized child," he was actually performing a tracheotomy on an eight-day-old infant... in a sewer, BTW. The baby was choking on a ping pong ball, which I seriously doubt would even fit in an infant's mouth much less be able to become lodged in its throat. I waited 35 years to read this story for the first first time today, and to be honest, I could have waited 35 more.
BATMAN 3D: [See "Joker" discussion for details.]
RUN, RIDDLER, RUN #1-3:
By the time Run, Riddler, Run was released I had yet to read Catwoman Defiant and Penguin Triumphant (and it would be another 33 years before I did). Also, I was in the midst of one of my periodic "cut-back" phases and was starting to realize that "buying new comics and not reading them is stupid." So I decided to give it a pass. Two years later, my LCS opened up its legendary backroom up for a quarter sale, and I bought issue #1 & 3 for 25¢ apiece. Mark Badger's art style didn't really appeal to me at the time, but I figured I'd buy #2 "someday." I never got around to it (although I see it is readily available today at less than cover price), but I read the two issues I have today.
The plot is about a housing development financed by the ultra-rich which will displace Gotham's poor. The title never really made sense to me, and now that I've read it, even less so. I mean, the Riddler's in it (out on parole), but he's not the main villain. In fact, he ends up working with the Batman in the end. I suppose the editor wanted a title that would have villain name-recognition rather than one that made sense. Plus, the Riddler doesn't really tell riddles; he tells jokes (in the "Did you hear about the [set up]?" variety, followed by the punchline). He does help the Batman navigate a series of death traps at the end (one of which is a giant prop typewriter), all of which much be solved by answering riddles. At the end, Riddler is returned to prison for missing a meeting with his parole officer. Eh. As with "Dark Knight, Dark City," I could have waited another 32 years to read this one.
BATMAN #490 - "Who Riddled the Riddler?"
We are now encroaching on what I think of as the end of the "post-Crisis universe" ("Knightfall," "The Death of Superman," "Emerald Twilight"). Bane and Jean-Paul "Whatsisname" are prominently featured, and B&R are wearing black Superman armbands. The Riddler sends a riddle to Commissioner Gordon: "What crowns just one but beats a dozen? Bim bam boom, some percussion." Don't try figuring it out; it refers to a bomb set atop the clock tower at Number One Gotham Plaza. Bane gets ahold of the riddle, arrives before Batman, and pumps the Riddler up with "venom." Riddler then goes on a super-charged riddle-spree with the following riddle: "It rises only where it's low, side poison chaining bottom to top it will go." Don't try figuring that one out, either.
HINT: "Side poison" = "poison side" or "Poseidon."
SHOWCASE '94 #3-4:
With Arkham Asylum destroyed in "Knightfall," its displaced inmates have been moved to Blackgate Prison. When the tension between the newcomers and the permanent residents reaches its boiling point, the Riddler, Two-Face, the Scarecrow, the Mad Hatter, Poison Ivy and the others seize the opportunity to get the upper hand... in a softball game.
1995 brought Batman Forever, and with the movie came a pair of one-shots (with diptych covers) featuring the cinematic villains: Two Face: Crime and Punishment and...
"THE RIDDLE FACTORY":
The Riddler is running a pirate TV game show targeting rich and famous roman à clef celebrities: Lady Godiva (Madonna), Harold Trojan (Donald Trump), Jeff Broom (Andy Warhol). The shows always end in tragedy for the celebrities, but what is the Riddler really after? This is perhaps my favorite Riddler story. It even references the Gaiman story from Secret Origins Special #1, my previous favorite Riddler story.
DETECTIVE COMICS ANNUAL #8:
Back on October 6 Captain Comics posted: "So the 'cheats at puzzles' bit is just a Golden Age artifact. Or will he still cheat when he returns?" I wouldn't have thought so, but by my count, the "cheats at puzzles" bit has been mentioned no fewer than four times since the Silver Age. This story is a pretty good summation of who the Riddler is (and recaps both his Golden Age appearances), but beyond that there's not much point to it. OTOH, if you've never read a "Riddler" story before, this would be a good one to start with.
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