Posted By Dan Greenfield on Aug 23, 2026 | 3 comments

AN ANNIVERSARY CONUNDRUM: The Prince of Puzzlers is just two years shy of 80…

The Riddler debuted 78 years ago, on Aug. 23, 1948, in the pages of Detective Comics #140. Created by writer Bill Finger and artist Dick Sprang (though Win Mortimer drew him on the cover), the Riddler was long recognizable for his bright green jumpsuit festooned with black question marks, and accented by purple gloves and belt.

It’s an unimistakable look.

So, why, I wonder, did longtime ’50s-’60s Batman artist Sheldon Moldoff color him orange in a series of paintings from (presumably) the 1990s?

Case in point (the first is from 1994, the other two are undated):

1994

Undated

Undated

Even Heritage Auctions, which sold these, said of the first illustration: “We’re not sure why the Riddler is wearing orange instead of his usual green — perhaps a nod to Jim Carrey’s wildly orange hair in the then-upcoming Batman Forever film? While we can’t confirm the creative thought process, we can say he appears to have the initial upper-hand on Batman and Robin as he topples a huge question mark statue toward them!”

They also mentioned that it was Moldoff who helped reintroduce the King of Conundrums in the Silver Age — specifically 1965’s Batman #171:

Inked by Joe Giella

So, he certainly should have known better.

And he did get it right in another illustration:

Undated

Well, whatever the reason, I’ll say this: Moldoff’s artistic instincts were still on the money, because the Riddler looks pretty groovy in orange! I’d love an action figure like that!

I guess it’s just a riddle for the ages.

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MORE

— THE RIDDLER Makes His SILVER AGE Splash: A 60th Anniversary INSIDE LOOK. Click here.

— 13 PANELS That Show THE RIDDLER Was Cool From the Very Beginning. Click here.