There are plenty of villainous characters on TV. You expect these bad guys to do dastardly things and antagonize everything. For every bad guy, there’s a good guy waiting in the wings to bring him down. But sometimes those two characters become one in the same, bending everything you thought you knew about a character.

Good TV characters take a walk on the bad side all the time. Whether it be over the loss of a lover, the need for revenge, or something ~magical~, there are plenty of reasons why good guys turn over to the dark side. Some of them make their way back to their roots, but some are seduced by the evil side of things and decide that’s who they are…

16. Piper Chapman, Orange is the New Black

Piper (Taylor Schilling) was a goody two shoes affluent New Yorker at the beginning of the series. Then she went to jail for the rebellions of her youth and although she went into the experience hellbent on staying the same person she’s always been, that became impossible. After being beaten down, attacked, and berated by her fellow inmates Piper has hardened considerably. While she was never wholly “likable” she was at least objectively good and didn’t want to get wrapped up in prison politics. But, whoops, then she did and basically decimated her outside life along the way. She ditched her poor fiance, broke her prison lover’s heart, and set her prison business partner up to get caught. Piper is still in the throes of her dark phase, so who knows what more time behind bars will bring?

15. Slade Wilson, Arrow

When billionaire playboy Oliver (Stephen Amell) finds himself trapped on an island after a boat crash he finds an ally: Slade Wilson (Manu Bennett). They had another ally, Shado (Celina Jade) with whom Slade was in love with her despite her feelings for Oliver. When enemies infiltrated the island, Oliver was forced to chose between Shado or his former love who also washed up on shore after the boat crash. His choice to let Shado die sent Slade into a violent spiral with his former friend as the target. Long after their time on the island, Slade reappeared in Oliver’s life as the villain Deathstroke and almost destroyed everything before ultimately being defeated, adding insult to injury since Slade trained Oliver to be the mercenary he is.

14. Theon Greyjoy, Game of Thrones

Theon (Alfie Allen) was never the hero type, but he wasn’t the TV show’s villain either. He just kind of existed in the Stark’s work as their ward, being raised by their father. He was strained between being a “Stark” and being a “Greyjoy” and ultimately decided to go back to his estranged family and help his father take over the North. This culminates in him taking over his former home, Winterfell, and murdering two innocent boys under the guise that they are Stark children. He’s eventually captured by the Bolton’s, tortured, and eventually reformed but not before he went real bad in his quest for power.

13. Bill Compton, True Blood

Vampire Bill (Stephen Moyer) was always a southern gentleman, especially when it came to his love for Sookie (Anna Paquin). But in the TV show’s fifth season he was taken in by the beliefs of the Sanguinista’s and ended up drinking the blood of villainess Lilith (Jessica Clark). His dip into the dark side led to him killing humans, destroying the Tru Blood factories, and creating a large conflict with the humans and vampires. He eventually found himself back working towards redemption before his death at the end of the series.

12. Ben Chang, Community

The TV show Community may be a comedy, but Chang’s (Ken Jeong) swift takeover of Greendale Community College is actually pretty serious. After forcing out the former Dean — and kidnapping him! — Chang takes over, leading an authoritarian regime. He has complete control over the school and the students and uses his power in cruel and unusual ways. From weirdo Spanish teach to complete Dictator, Chang really took his quest for power in a crazy direction. He eventually resets his life: by faking amnesia so people like him again.

11. Quinn Perkins, Scandal

Quinn (Katie Lowes) was a little lost, but wholly good when she joined OPA on a quest to help the helpless and fix problems in Washington. After spending some time at OPA and learning from Huck (Guillermo Diaz) on how to hack, track, and torture people, she starts to love the high that comes from the acts. She meets future fiance Charlie (George Newbern), a member of the mysterious and brutal B613, and ends up diving into his life as she becomes more and more bloodthirsty. Huck eventually tortures her back to the good side (naturally), where she’s started to have a somewhat normal (and baby-filled!) life with Charlie. She now even leads OPA herself!

10. Tom Keen, The Blacklist

Tom (Ryan Eggold) seemed like a loving husband and great match for Liz (Megan Boone) — that is until we learn his entire life has been a lie. He was hired to watch over Liz but ended up falling for her and perpetuating an entire fake identity through their life together. His constant lies to Liz turned him into someone she literally did not know and contributed to all the things that completely destroyed her life when she started at the FBI.
Their love for each other never faded, though, through all the shootouts and double crossings. Eventually, he finds a way to be honest with her and they find their way back together in one of the most messed up relationships on TV.

9. Dean Winchester, Supernatural

Dean (Jensen Ackles) has always been a good-natured demon hunter with love for his brother. That is until he becomes a demon himself. In the tenth season, Dean is taken over by a demonic force and turns into all the things he hates. He even tries to kill his brother! Luckily his brother didn’t take it personally and ends up saving Dean in the end, ridding him of the evil within him. I guess that’s the risk you take when you mess with the supernatural!

8. Jenny Humphrey, Gossip Girl

Jenny (Taylor Momsen) was Little J, just a girl living on the Upper East Side wanting to be popular. That quest for popularity leads her down a dark path, though, and her good girl demeanor soon fades as she does anything to be on top. She tarnishes friendships, takes down her former friends, and actively works to humiliate people in public. She basically turned into a mega-bitch. Luckily she eventually leaves the Upper East Side, seeing that it was turning her into a bad person.

7. Lex Luthor, Smallville

The TV show Smallville tells the story of Superman’s origins, so Lex (Michael Rosenbaum) going bad is inevitable. While he begins the series as a close friend of Clark Kent’s (Tom Welling), the two find themselves at odds as the series goes on. Through circumstance and time, Lex becomes a much darker character. He feuds with his father and finds himself at odds with most women in his life. His narcissism and eventual memory loss leads him to fulfill his destiny as Clark’s enemy — but we all know what happens to those who go against Superman since, you know, he’s a superhero and all.

6. Regina Mills, Once Upon a Time

Regina (Lana Parilla) is the show’s actual Evil Queen, so her trips to the dark side are predictable and frequent. She begins the series as the “big bad” hellbent on ruining Snow White and Prince Charming’s lives. Through time, curses, and children, Regina becomes a kinder force and eventually finds herself on the side of the good guys. That is, of course, until a new curse sends her careening back into evil. The back and forth has happened a few times, with her usually finding her way back to good for the sake of her son. But on Once Upon a Time, anything can happen.

5. Angel, Buffy the Vampire Slayer

Angel (David Borneaz) was a tortured vampire. He tried to resist his nature so vehemently and live a decent life to make up for the sins of his past after being “cursed” with a soul. Unfortunately for him, falling in love and having a moment of “true happiness” threw him back into his evil nature when he loses said-curse. Turns out he was supposed to suffer his life away if he didn’t want to be evil again, whoops! Evil Angelus is unbelievably cruel — especially to his love Buffy (Sarah Michelle Gellar). His plan to destroy the world is even looked down upon by his evil peers! Eventually, Buffy vanquishes the evil Angel and sends him to hell — only after Willow curses him with a soul again. He comes back from hell eventually but winds up moving to LA when he realizes life for Buffy will be better without having him as a temptation. After all, they can’t experience ~true happiness~ ever again.

4. Nancy Botwin, Weeds

Nancy (Mary-Louise Parker) was willing to do anything to support her family after her husband died. Including selling drugs. What started as some minor pot-selling turned into a drug empire. Nancy slowly became a kingpin, moving from naive beginnings to cruel leadership. The woman who would do anything for her kids actually ends up messing them up with her “business” ventures. By the end of the series, Nancy tries to make up for her mistakes with her kids with her youngest son, but she’s ultimately left lonely by those around her. Become a drug lord, lose your family. Tough breaks, Nance.

3. Stefan Salvatore, The Vampire Diaries

Stefan’s (Paul Wesley) “ripper” past is well-documented — he ate an entire town once! But in modern times, he was making concentrated efforts to be a “good” vampire. That is until he’s blackmailed into turning his humanity switch off and turns back into Ripper Stefan during the TV show’s third season. He goes on a total blood binge, killing everything in his way. He eventually is able to be saved and turned back into the noble Stefan we know and love. He’s forever changed, though, and spends a lot of guilty years trying to make up for his evil streak.

2. Walter White, Breaking Bad

When the title of your TV show is Breaking Bad you can bet some good guys are going to break bad. Walter was a well-mannered, and kind of pathetic, science teacher at the beginning of the series. When he’s diagnosed with cancer, he decides to do the unthinkable to provide for his family: cook meth. He figures it’ll be perfect — he’s smart enough to do it and has no interest in indulging in the drug. Unfortunately, there is no easy way to be a drug kingpin. He’s pushed farther and farther into the darkness until he becomes cruel and unrecognizable. As he tells his wife, he’s not someone who gets shot when an enemy knocks on the door — he’s the one that knocks. Walt ends the series a shell of who he once was, losing everything with his walk on the wild side.

1. Willow Rosenberg, Buffy the Vampire Slayer

When Willow’s (Alyson Hannigan) love Tara (Amber Benson) is killed, she goes off the rails. The benevolent and kind-hearted witch loses herself in her grief and to an addiction to dangerous magic. Dark Willow vows to exact revenge on the Trio that murdered her love and then seeks to destroy the world in vengeance. She’s eventually saved by her best friend, Xander (Nicholas Brendon), who uses their love and friendship to talk her out of her plans. While her friends forgive her because Willow has never done something maliciously before, she struggles with forgiving herself for quite a while.

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