The 25 greatest Gotham villains of all-time

1. Oswald Cobblepot (Penguin)

Portrayed by: Robin Lord Taylor

First appearance: “Pilot”

Oswald Cobblepot is one of the longest-lasting villains on the show and that gave him the upper hand in earning the top spot. He can be annoying at times, but he’s still dangerous. Eventually, he ends up being the Mayor of Gotham, which gives him more power than he should be able to have as a criminal.

I’ve also mentioned him in a lot of the previous entries here, which should tell you something about his survival skills. He’s escaped death and been able to thwart other villains who stand in his way. Sofia Falcone gave him a run for his money until Lee Thompkins put a bullet in her head.

Oswald has always been able to get people to work with him. Victor Zsasz has done a lot of work for him and he’s always able to convince others like Butch and Mr. Freeze to do his dirty work, too. The Penguin is just always there and because of that presence, he’s always scheming. It’s hard for him to be content, which is what allowed him to work his way up to becoming the Mayor of Gotham in the first place.

Despite his constant presence, he’s suffered a lot. He lost his mother, tried to reconnect with his father and even found himself on the brink of death a few times. Each time, he’s bounced back and made a bigger name for himself. Something he kept going right up until the end!