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.

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The Riddler would also appear in Super Friends #4 (Ap'77) and join the Legion of Doom in 1978's "Challenge of the Super Friends"!
I was aware of the Riddler's appearance in Super Friends #4, but wasn't planning to deal with it here since it's not canon. I have it, though, and flipped through it just to see if there's anything worth mentioning. There's not really, except this particularly lame riddle: "Why is 'Wendy' such an unusual name?" Robin concludes it is unusual "because the end comes in the middle," but much more interesting is the fact that the name was coined by J.M. Barrie in 1904 to be Peter Pan's "friendy-wendy."
BATMAN #317:
the Riddler breaks jail and the first thing he does is to send Batman a book of riddles c/o the GCPD. the second thing he does is to hijack a truck carrying a load of chickens. the third thing he does is to back a garbage truck up to a warehouse loading dock. Inside the "garbage truck" are the chickens, which cause enough of a distraction that he is able to steal a shipment of magazines intended for foreign distribuition. Oddly, the dock-workers are armed and begin firing at the Riddler's truck as he drives it away. Attracted by the gunfire, the police discover that the warehouse is a front for a gun-running operation.
Meanwhile, Robin has gone to the state pen to see what he can learn about the Riddler's escape. He finds the Riddler's cellmate, a gunrunner who was injured during the Riddler's escape, in a "semi-comatose" state. That goes nowhere, so he returns to the Batcave. The point of this latest crime spree is to give new meaning to old riddles, but I'm not in the mood to relate his lame clues or explain how they tie into his crimes today. Apparently Batman isn't either, as he ignores the riddles in the book and catches the Riddler using plain, old-fashioned detective work. (The guns were hidden in the magazines and Batman caught up to the Riddler at the harbor as the guns were being loaded aboard a cargo ship.)
Robin's final question to the Riddler: "Why are you like a spawning salmon?"
DETECTIVE COMICS #493 - "Riddles in the Dark"
The Riddler's men have sprung him from jail. He plans to leave Gotham, butwithin six hours of gaining his freedom, he has already lured Batman to discover the riddle detailing his escape route he is compelled to leave: "Why is a cook's brain pan like an overwound clock?" It is Alfred who identifies it as an unanswered riddle from the Gilbert & Sullivan operetta Yeoman of the Guard. The riddle has no answer, but the clue is the riddle itself. In the operetta, the question was asked by the jester Jack Point, and there is an airfield ay Jackson Point near the edge of the city.
Batman takes the whirly-bat in an effor to head him off. He's too late, but he does manage to throw a trace onto the Riddler's plane. The Riddler drops another riddle from the plane on a little parachute: "When is a horse most like a stamp collection?" Because of the tracer, Batman knows in which direction the Joker is heading anyway, but the clue narrows his destination down to Houston's Hobby Airport. The Batman was able to beat him there, but still failed to nab him. He was assisted by Michael Carter, a local hero a.k.a. "The Swashbuckler." (Carter's uncle is Greg Sanders, the Vigilante.) Before getting away, the Riddler shouted another clue: "Who is a greater Riddler than I?"
Batman saw the license plate of the Riddler's getaway car, and the Swashbuckler helped him track to a nearby trailer park, where the Batman finds himself in a situation so lame I hesitate to call it a deatrhtrap: he's "trapped" inside a trailer the Riddler has set afire and escape by removing a panel covering an aperture meant for a window air-conditioning unit. He tracks Riddler to the Astroworld amusement park, but loses him there. Later, Batman and the Swashbuckler try to solve the Riddler's last riddle. Swashbuckler thinks it might refer to a showhorse named "Conundrum" which he could hold for ransom, but Batman thinks it refers to a solid gold statuette of the Sphinx which oil millionaire J.R. Noone is donating to the museum.
So while Swashbucler heads for the horse show and Batman heads for the museum, Riddler is patting himself for his ingenuity in misdirecting both of them as he heads to the home of J.R. Noone. When he arrives, though, he finds Batman himself disguised as the millionaire. At the last minute, Batman deciphered the real answer: that "No/one" is a greater riddler than he. The Swashbuckler hets the final zinger: "What did the pig say when the farmer grabbed him by the tail?"
The Riddler supplies the answer: "This is the end of me!"
The art for this story is by Don Newton. I had some of his Phantom comics when I was kid, but he didn't really enter ny radar until he became the regular artist on Infinity, Inc... then passed away. Today, in this new Golden Age of Comics, all of Don Newton's Phantom stories and all of his Batman stories are available in handsome HC collections.
I was stoked to get Detective Comics #493 because it had the Red Tornado's first solo story in the "Tales of Gotham City" feature. Don Newton would also draw the Batman/Red Tornado teamup in Brave and the Bold #153 the previous year.
The Swashbuckler was a quaint one-shot hero with a generic costume, memorable only for his connection to the Vigilante. In fact, the story would have been more interesting had the Vigilante been the guest star!
THE BRAVE & THE BOLD #183 - "The Death of Batman"
Batman is teamed with the Riddler to solve a crime by a "mystery" villain, amateurishly written by someone named Don Krarr. The "mastermind" is evident by page three.
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