Edward Nigma, the boy who would grow up to be the Riddler, had a criminal bent at an early age.  His first foray into deceit  came in school, when he cheated to win a prize solving the class puzzle.  Stimulated by the win, he developed a knack for presenting “unsolvable” riddles which he could solve with hacks he had created in advanced.  After school, he made a living for himself running street rackets as “the Puzzle King” but felt he was insufficiently challenged by fleecing ordinary citizens.  Much greater reward, and invigoration, would be found in defeating the Gotham Police or even Batman.  He resolved to create a new criminal identity for himself and thus was born …. The Riddler!

The Riddler’s  first crime involved hijacking a new advertisement – a lit up cross word – to introduce himself and challenge Batman with three clues – A water vessel, a public way and a formal dinner.  The Dynamic Duo guessed the answers – a basin, a street and a banquet – but jumped to the wrong conclusion that the Riddler was robbing a banquet on Basin Street.  Instead, he flood the bank on Basin Street and robbed it underwater (bank-wet).  In his second clue the Riddler makes the police solve a jigsaw puzzle that he says he will rob the Eagle’s nest.  While Robin heads to a rooftop club called the Aerie, Batman checks an alternative theory, that the Riddler is robbing the home of millionaire Hamilton Eagle.  Batman’s suspicions are confirmed but the Riddler has left Eagle in a puzzle-based death trap that Batman had to solve while the Riddler escaped.  In the final puzzle, the Riddler asks why his corn hard to escape?  The answer – because its maize (a maze) – lures Batman and Robin to a glass maze on the water front that the Riddler has blocked the exits after the enter and laden with bombs.  With minutes ticking down, Batman breaks through one of the walls and escapes as the explosion throws Riddler to his apparent death (Detective Comics #140).

The Riddler had not died however, having swam into a drain pipe and re-appeared a few months later with new schemes.   He crashes a puzzle contest and captures the presenters in a wire mesh puzzle, fleeing with the prize money.  The idea gives me an idea – he will engage the public in his next brazen crimes to create confusion to cover his thefts.   He use the power controls of a skyscraper to write out a riddle in the windows – a heavy wagon and a furnace.  Batman and Robin rush in on the Riddler but he had jigsawed the floor which collapses beneath their weight.  The public guesses the clues – a heavy wagon is a cart and a furnace is a heater and thus they flock to a drive-in – a cartheater.  In the mob, the Riddler leaves $1000 to be found by the crowd but steals $5000 from the box office and escapes on a motorcycle. Batman and Robin can’t follow through the jammed cars.

The Riddler’s second puzzle was announced from a blimp towing the clues – a rein, a bow and a club.   Batman and Robin swoop in on the Bat-Plane but the Riddler sabotages the blimp and parachutes away, leaving the Dynamic Duo to deal with the crashing blimp.  The crowd below solves the puzzle – The Rainbow Club –and rush off to the next prize.       Batman and Robin intercept the riddle but again he parachutes from atop a giant sign and uses the crowd to escape.  The final clues are given when the Riddler crashes a TV broadcast and offers four hints – that he’s got a ham, he mews like a cat, he stares into the distance and he hums a tune.  Batman deduces that it spells out Gotham Museum.  The Riddler steals jewels and when the heroes arrive, slips into a hall of mirror.  Batman recognizes that reflections are always reversed and only the real Riddle will have his question marks showing the correct direction.  He lunges for that figures and the Riddler is bound and sent to jail (Detective Comics #142).

The activities of the Riddler after this point are unrevealed.  In the early 21^st century, the aging Joker mourns that the Riddler has died, indicating his passing and that he knew the Joker, the circumstances of which are not known (JSA Annual #1).   How he died, if he is truly dead and whether he left heirs is unknown.