The 25 greatest Gotham villains of all-time

GOTHAM: L-R: Robin Lord Taylor as Oswald Cobblepot / Penguin, Cory Michael Smith as Edward Nygma / The Riddler, Donal Logue as Detective Harvey Bullock, Ben McKenzie as Detective James Gordon, David Mazouz as Bruce Wayne, Chris Chalk as Lucius Fox, Camren Bicondova as Selina Kyle / the future Catwoman, Sean Pertwee as Alfred Pennyworth and Erin Richards as Barbara Kean. Season 5 of GOTHAM premieres Thursday, Jan. 3 (8:00-9:00 PM ET/PT) on FOX. ©2018 Fox Broadcasting Co. Cr: JUSTIN STEPHENS / FOX
GOTHAM: L-R: Robin Lord Taylor as Oswald Cobblepot / Penguin, Cory Michael Smith as Edward Nygma / The Riddler, Donal Logue as Detective Harvey Bullock, Ben McKenzie as Detective James Gordon, David Mazouz as Bruce Wayne, Chris Chalk as Lucius Fox, Camren Bicondova as Selina Kyle / the future Catwoman, Sean Pertwee as Alfred Pennyworth and Erin Richards as Barbara Kean. Season 5 of GOTHAM premieres Thursday, Jan. 3 (8:00-9:00 PM ET/PT) on FOX. ©2018 Fox Broadcasting Co. Cr: JUSTIN STEPHENS / FOX /
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Gotham on FOX. ©2019 Fox Media LLC Cr: FOX /

5. Edward Nygma (The Riddler)

Portrayed by: Cory Michael Smith

First appearance: “Pilot”

Edward Nygma had a long run as a villain on the show. He didn’t start out as one, but his journey to becoming The Riddler was obvious from the start. As soon as you hear his name, you know what’s going to happen, but not necessarily how. It wasn’t his immediate intention to become a criminal, but it happened while he was working at the GCPD.

While working at the GCPD, Nygma starts dating Kristen Kringle, who was the Record Keeper there. He winds up killing her (this one is actually by accident) and we begin to see his dual personality. There’s Edward Nygma and then there’s The Riddler. He tries to frame Jim Gordon for Kringle’s death, but finds himself being sent off to Arkham instead.

Edward wore many hats throughout the show. After getting out of Arkham, he worked for Oswald Cobblepot on his campaign. When Oswald killed his new girlfriend, though, he formed an alliance with Barbara Kean, Tabitha Galavan and Butch Gilzean to get back at him. Oswald manages to put him on ice, causing brain damage when he’s later thawed out.

Despite the brain damage, Nygma started to get his Riddler persona back and started to participate in an underground fight scene in the Narrows with Solomon Grundy (Butch) as his fighter. He was still quite the manipulator, but Lee Thompkins knew that he wasn’t the same man he was before.

In “No Man’s Land,” The Riddler was taking over a little more and he was able to abduct Jim. An attempt to try to get Lee to do something she didn’t want to do resulted in him being stabbed. Fortunately, Hugo Strange saved the day allowing The Riddler to re-emerge in the show’s final season and reach his fully realized potential by the show’s final curtain call.