10 Most Embarrassing Moments For Comic Book Villains

10. Every Time The Riddler Loses (Take Your Pick)

Batman War of Jokes
DC Comics

Although the Riddler is one of Batman's most formidable and most renowned antagonists, he's also a bit of a sore loser. Always impeded by a compulsive need to leave behind riddles that'll lead Batman to him once they're solved, Eddie is his own worst enemy.

As such, it's pretty difficult to pin down just one moment where he was left red-faced, let-alone embarrassed. If we were to pick a recent example, however, it would be from the finale to Tom King and Mikel Janín's The War of Jokes and Riddles, where the punchline - delivered by Riddler - falls flat.

Having orchestrated the meteoric rise of Kite Man from C-lister to A-lister in an attempt to get the last laugh, so to speak, over his purple clad adversary, Nygma found himself at a loss when the joke didn't get the desired effect. With Riddler having also murdered Kite Man's son in an attempt to orchestrate the character's rise, even the Clown Prince himself failed to see what was so funny.

As far as indictments go, that's pretty fierce. Considering the Joker's entire motif is to clown around, the lack of laughter on his behalf stung Nygma far worse than any Bat-gloved fist to the face ever could.

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WhatCulture's very own resident movie guy, Ewan has been working in the content creation biz for over 10 years now, having started as a freelance contributor to WhatCulture Gaming all the way back in 2015. After graduating with a First-Class Honours in History from Northumbria University in 2017 (where he won a prize for a totally killer dissertation on the Watergate years), Ewan took on the role of Comics Editor at WhatCulture and quickly developed WhatCulture Comics into one of the biggest superhero-focused channels on YouTube. He followed this with a brief hiatus at Screen Rant in 2021, where he worked across the Gaming and Film sections as a writer and editor, before returning to WhatCulture as a Senior Content Producer / Presenter in 2023. He started his own podcast, We Love Dad Movies, in 2022, and has contributed several written pieces to the Eisner-nominated comics website Shelfdust as well. In his current role, Ewan incorporates his love of cinema, comic books, and history into written pieces and video essays for WhatCulture's Film & TV channel, as well as WhatCulture Gaming and WhatCulture Horror, with a particular focus on nineties-era Dad Movies, old school Westerns, and Golden Age Hollywood Noir. John Carpenter is his fave, and he thinks Batman Beyond should never have been cancelled. If that's your vibe, you'll probably like his stuff.