The 20 Biggest Anti-Heroes and Why We Love Them

9. Omar Little – The Wire

Played by Michael K. Williams

If we’re gonna talk about anti-heroes, there is absolutely no way we won’t include Omar Little in the list. Notoriously known for being a stick-up man in Baltimore, he often robs street-level drug dealers. He is so notorious that when he walks, people would run away and warn others, saying “Omar comin’!” Despite this, he adheres to a strict personal moral code, including not hurting innocent people and not using profanity.

‘The game’s out there, and it’s play or get played.”

10. Daria Morgendorffer – Daria

Voiced by Tracy Grandstaff

It’s incredibly easy to look beyond Daria’s drab outfits because of her intellect and wit. Her monotony cements her grim and sardonic personality, making her an icon. She can be completely pessimistic and cynical, but then again, who doesn’t know at least one sarcastic teenage girl? She might be anti-cheerleader and anti-everything, but she doesn’t have low self-esteem!

“My goal is not to wake up at 40 with the bitter realisation that I’ve wasted my life on a job I hate because I was forced to decide on a career in my teens.”

11. Al Swearengen – Deadwood

Played by Ian McShane

Al Swearengen is an “entertainment entrepreneur,” which could be just a euphemism for “pimp.” He owns Gem Saloon, which offers alcohol and prostitution. He was one of the first settlers of Deadwood, earning him influence and a position of power. He is cunning, manipulative, and is also said to by cynically amoral. Even though he is portrayed to be a cutthroat criminal, he shows a complex personality through his loyalty and sense of affection to a chosen few.

“God rest the souls of that poor family…. and pussy’s half price for the next 15 minutes!”

12. Crowley – Supernatural

Played by Mark Sheppard

He is the King of Hell. His mother is a witch. He tries so hard to be bad, but he has a nice streak that just won’t quit. He loves a good pun or two, and even though he is meant to be a demon-fueled hell-running devil, he’s just a plain nice guy that wants to make friends.

[voicemail message] “Too busy inflicting pain to answer. Leave a message.”

13. Captain Jack Sparrow – Pirates of the Caribbean

Played by Johnny Depp

Probably the most infamous pirate in the movie world (and that’s saying a lot because, well, pirates…), Captain Jack Sparrow is extravagant and oftentimes ostentatious. Despite being a pirate, he dislikes using force. Instead, he prefers to use wit and cunning in negotiating with his enemies. But then again, when slyness does not work and fleeing is not an option, he does not hesitate to give a good fight.

“Me? I’m dishonest.. and a dishonest man you can always trust to be dishonest. Honestly. It’s the honest ones you want to watch out for.”

14. Betelgeuse – Beetlejuice

Played by Michael Keaton

Getting the funny sounding name out of the way, Betelgeuse is a miscreant ghost who is a freelancing “bio-exorcist,” whose job is to get rid of humans. He was hired by the Maitlands, Adam and Barbara, who are both newly minted ghosts to scare off the family living in the house they owned before they died. But with Betelgeuse’s crude, morbid, and offensive behaviour, he easily wreaks havoc on the neighbourhood.

“I’ve seen The Exorcist about 167 times and it keeps getting funnier every single time I see it!”

Next Page: More Anti-Heroes That We Love