In Catwoman: When in Rome, he joins Selina Kyle on a trip to Italy in search of his fellow rogue's origins. It is there that he manipulates her into believing that some of Batman's most dangerous foes are after her. He has his henchmen employ several gimmicks and weapons used by the Scarecrow, Mr. Freeze, and the Joker to achieve this. He hopes to extract Batman's real identity from her, but to his dismay, she actually doesn't know or care. The Riddler appears in The Question series, being convinced to become a "big-time villain" by a prostitute he meets on a bus. He hijacks the bus and begins asking riddles, killing and robbing anyone that gets them wrong. The Question quickly subdues him by asking him philosophical riddles in return. He is outwitted and has a mental breakdown before being set free as a reward for getting one last riddle right.
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