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 /

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17. Theo Galavan

Portrayed by: James Frain

First appearance: “Rise of the Villains: Damned If You Do…”

While we just went through the Order of St. Dumas, Theo Galavan played more of a role than that. He became Azrael in later episodes and his character died more than once, which is always worth mentioning (and seems to happen a lot in Gotham).

Theo and Tabitha were essentially hitmen for the Order of St. Dumas when they were sent to Gotham. Their goal was to kill Bruce Wayne, which failed because we all know he becomes Batman and you can’t kill him off before that ever happens. Theo even becomes the Mayor of Gotham at one point, too, although it only lasts briefly.

Oswald Cobblepot brings the demise of Theo Galavan, however, his story continues as Hugo Strange reanimates him. Indian Hill gave him a new life as Azrael and then Strange convinces him to go after Jim Gordon. When he goes after Jim, he sees some of his old campaign posters and it’s clear that Strange didn’t completely wipe his mind as the memories start coming back to him.

It took a rocket launcher to get Theo Galavan down for the second and final time. His memory of wanting to kill Bruce came back, which drove him to Wayne Manor. Bruce hit him with a car, he was shot and when he still didn’t go down, Butch Gilzean showed up with a rocket launcher. Theo had a pretty good run, but it had to come to an end.

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