Welcome to House of List-ery: Fashion Files, where we present our candid assessment of an iconic DC character’s bravest and boldest fashion choices. This month, the Riddler is getting a graphic novel of his own with Batman - One Bad Day: The Riddler. But does Eddie Nygma have One Bad Outfit? We’ve raided his closet from the Golden Age to his latest to find out. We’ll rate every outfit out of five question marks, with an exclamation point for half-marks.
The Sprang Original
Detective Comics #140
Dick Sprang’s unique Batman designs for the Caped Crusader and his allies, his enemies, and the city itself may have been the first to grant Gotham its signature look. But when it comes to character, no design of Sprang’s quite captures his savoir faire as the Riddler. Give or take the number of question marks on the green leotard cinched with a stylish purple belt, there’s a reason this design persisted through most of the 20th century and onto Frank Gorshin in the ‘60s Batman TV series. A high bar from the start.
Dark Knight, Dark City
Batman: The Animated Series is often credited for switching Riddler’s signature look from a green body sock to a smart blazer, but the comics got there first with Peter Milligan and Kieron Dwyer’s “Dark Knight, Dark City.” The arc is better remembered for introducing the demon Barbatos into the Batman mythology, but it’s also worth noting as the signal for Riddler’s fashion evolution. Bit too much purple, though. Future iterations of the suit will tone that down.
The Bruce Timm, Mark 1
The upgrade from blazer to suit pays off from his “Dark City” incarnation, as does the elegant simplification of the question mark motif to a single punctuation on his tie. Not necessarily better than Sprang’s first draft, but a lateral move for sure.
A return to Sprang form—or perhaps, we should say, Gorshin form—for this campy tribute to the ‘60s Batman TV series. Honestly, it’s missing the belt to break up all that green.
The Bruce Timm, Mark 2
For The New Batman Adventures, Riddler went through a redesign apparently influenced by Batman Forever’s change in visual direction. It maintains the understated use of the question mark motif from animator Bruce Timm’s previous design…but we still miss that belt.
The Tim Sale
Nothing wrong with a Tim Sale design. The combination of bowler hat, bowtie and dark slacks makes Sale’s hapless Riddler feel like a wretched little nerd playing cops and robbers in a club which never really accepted him as a member, which is exactly the feeling he’s meant to convey. Sale was one of the greats for a reason.
Night on the Town
Green Arrow #12
Many versions of Riddler’s suit design make the mistake of overdoing it on the purple. But Phil Hester’s work on Ridder’s classy tuxedo shirt and dark, thick lapels set off that bold tie quite nicely here, like he’s put on his best for a night to remember.
Kiss the Genius
Batman Adventures #11
No explanation necessary. Perfection.
Scourge of Star City
Green Arrow #35-37, #49-50
Writer Judd Winick’s tenure on Green Arrow is a favorite among Arrow Family fans for a quiver full of reasons. But one of his most interesting choices was taking a B-List Batman villain and reshaping him into Star City’s greatest villain. Visually, this run refined the many variations of the Green Suit Riddler into his finest form, transforming Timm’s dressed-down Batman: The Animated Series vision into a visual treat for the comic medium. Not too much purple, visible question marks without being too busy, question mark cane, suit, bowler hat, gloves. Pure style.
Riddle Me That
Riddler underwent a drastic, dress-down makeover in 2004’s Legends of the Dark Knight storyline “Riddle Me That,” with a gothic flair, a motif constrained down to a neck tattoo, and a demand to be taken seriously. It’s not offensively bad, but it is a little boring. Which, when you’re talking super-villain costumes, is almost worse than bad. The look would be abandoned after Riddler got amnesia in Infinite Crisis, after which point, he retreated to his rack of green suits.
Speaking of the bad ones, though.
As gorgeous as Alex Ross’s art is to behold in any form, we have to confess that this trenchcoat look would be criminally bland under the pen of any other artist. You couldn't even tell it was the Riddler without the question mark cane, and he appears to have stolen the Corinthian's glasses.
Riddler wore a number of variations on his trademark suits over the course of his reformation period from 2006-2011, all of which average out to about a 7/10. But we’d like to single this one out from the Gotham Underground series in particular for the missed opportunity of question mark cufflinks.
This is a look, all right. The Riddler’s no angel in this standalone graphic novel from Brian Azzarello and Lee Bermejo, but the real criminal here is his tattoo artist. Hopefully Batman caught him because he cannot be allowed to remain at large.
The ensemble for Riddler’s return to supervillainy feels like it tried to combine successful elements from previous Riddler designs, marrying the Sprang classic to an updated suit, but it ends up looking like a disturbing hodgepodge. Which we suppose is appropriate for the story, where Riddler himself appears to be losing it.
Riddler in the Dark
Legends of the Dark Knight #53-55
A fairly standard Riddler look, save for that double question mark-shaped domino mask. A daring choice, but one that doesn’t quite work. (More like “Accessorizing in the Dark.” Zing!)
Batman: Zero Year
Okay, okay, okay. We get it. Of course, Riddler would wear a fedora. Of course, he would grow those muttonchops. Of course, he’s the guy who will challenge you if he spots you wearing a Batman shirt to name your top five comic book artists. The look is rancid, but it serves its purpose well: this is a man you are meant to hate.
Hey, remember all those debunked rumors that David Tennant was going to play the Riddler in The Dark Knight Rises? Because Rocksteady Studios sure did. Impossible for us to rank without bias because we are in love with this awful goblin.
War of Jokes and Riddles
If we’re not mistaken, this play on Azzarello and Bermejo’s Joker design by Tom King and Mikel Janin is equally inspired by an emotionally gut-wrenching scene in Paul Dini’s autobiographical Dark Night: A True Batman Story. We commend them for swinging for the fences, but at the end of the night we’re still being forced to look at bare-chested Riddler. Button it up, Eddie.
Dark Nights: Metal
Teen Titans #12
We’re going to chalk this one up to the corrupting influence of the Batman Who Laughs. He looks the part for the story, but we’d be just fine if we never had to see him looking like this again.
Their Dark Designs
An interesting update on the Sprang classic married to the crossword puzzle aesthetics of Scott Snyder’s Riddler interpretations, but in execution feels a little too ordered. Sometimes an outfit that’s true to the character lacks the punch needed for the reader. Still, it’s almost there.
And here’s our latest, fresh from theaters and currently streaming on HBO Max. Look at this thing. It’s awful. Zero craftsmanship. Frightening to look at. Truly the work of a diseased mind. Admittedly pretty cool lapel logo. This is, objectively, the least flashy and fashion-conscious costume the Riddler has ever worn, but we can’t help but admire it because it’s simply so intentional to the themes, messaging and character of the film itself. We award this costume a single interrobang, with our highest honors. This is truly The Riddler’s One Bad (or maybe badass) Outfit.
DC House of List-ery runs every Thursday here on DC.com.
Batman - One Bad Day: The Riddler by Tom King and Mitch Gerads is now available in print and as a digital comic book.
Alex Jaffe is the author of our monthly "Ask the Question" column and writes about TV, movies, comics and superhero history for DCComics.com. Follow him on Twitter at @AlexJaffe and find him in the DC Community as HubCityQuestion.
NOTE: The views and opinions expressed in this feature are solely those of Alex Jaffe and do not necessarily reflect those of DC Entertainment or Warner Bros.