The amount of good in the world that the Winchesters do in Supernatural is incredible. From saving families to each other for the world, they have their problems, but they are certainly heroes. Even as individuals, they do a lot of good. Dean is as concerned as he sounds, but his selflessness, care, and skill lead him to perform a series of heroic acts over fifteen seasons of the show.

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However, alongside these heroic acts, Dean can find himself doing wrong, making mistakes, and being more villainous than heroic, either because he’s not in control or because he mistakenly believed he was doing good, something that Sam and Cas were also. guilty. .

10 Hero – Killing Eva

Eve is a villain who disappointed many. Despite her status as the Mother of All, she didn’t have much of an impact and died pretty quickly never to return to the show again. However, Dean killing her was quite heroic and was a risky move on Winchester’s part.

To kill the mysterious being, Dean ingested Phoenix’s ash with a sip of whiskey and prompted Eve to bite him, to which she was forced by trying to turn them into monsters, which she was later killed when she was poisoned by Phoenix’s ash in her blood. A bold move even by Dean’s standard.

9 Villain – The plan to kill Amara

Dean and Amara / the Darkness have this strange cosmic bond that means they can’t really hurt each other. However, that doesn’t mean Dean can’t lie to her and send her to her death, which is exactly what he does.

He lies to Amara about having a way to trap God and asks for her help, which she eventually gives him, trapping Chuck waiting for the Winchesters. When she discovers that Dean lied and had planned for Jack to kill both her and God, her heart is broken and God absorbs her.

8 Hero – Bringing Cas back from Naomi

Castiel is a character who always gets into trouble and desperately tries to do good while actually doing the opposite, sometimes being manipulated by others to do things against his good-hearted nature, others like Naomi.

After a long time of Naomi basically controlling Castiel, it was time for her to kill Dean. Dean being Dean, he doesn’t give up on Castiel or the good in him and manages to bring the real Cas back through his heart and will, and Cas finally realizes what was really going on.

7 Villain – Constant Lies To Sam

The Winchesters have serious trouble lying to each other. It is practically a constant in the program that one of the two hides something or lies about something to the other.

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Dean tells Sam a lot of lies that are sometimes quite harmless and unnecessary, but that do not cause much damage, but some end up having consequences, such as lying about Gadreel, which causes Kevin to kill. There are also things like him selling his soul (which didn’t last long) and hiding the effects of the Mark of Cain.

6 Hero – Erasing Lisa and Ben’s memories

Dean’s apple pie year of life with Lisa and Ben was about the closest he got to a family of his own and a normal life away from hunting, but it was never going to last.

When Sam returned, that life began to end. As they tried to make it work with hunting Dean, it soon became clear that that couldn’t happen. To protect them, Dean made the decision to erase her memories of him, a heartbreaking decision that took so much strength from Dean.

5 Villain – Kill Amy

Amy’s pond Supernatural He didn’t have as much of an appetite for fish sticks and custard as the character in another franchise, even more so a natural appetite for brains being a Kitsune.

Amy was an old friend of Sam and did not kill humans. Instead, she fed on dead brains and supported herself for years until her son needed more sustenance, and she killed people she felt deserved to let her son survive, and when she told Sam the truth, he left her. to go. But, Dean caught up with her and her son, and killed her for her actions, warning her son that if he killed, Dean would kill him too. It was definitely a dark and unpopular Dean moment.

4 Hero – Killing Azazel

Sam, Dean, and John’s primary focus during the first and second seasons of Supernatural it was to hunt down and kill the demon that killed Maria. That was “yellow eyes”, also known as Azazel, a prince from hell.

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It took a lot of hunting, and the trip saw a lot of ups and downs, including Sam, Dean, and John dying somehow, two demon deals, and Dean’s life was shortened to a year after a demon settlement, but they did. . In the season 2 finale, Dean shot the Colt and killed Azazel once and for all.

3 Villain – Killing Cyrus

Dean kills Cyrus Styne after he pleads for his life in Supernatural

The Styne family was a short-lived but shocking family of minor villains who caused the Winchester brothers a lot of trouble and killed Charlie. But Cyrus Frankenstein was different; he hated his family and did not want to join them.

However, he was still too young to make the journey on his own, so his family forced him to do things, including going to the Bunker. There, Dean arrived after killing his entire family and killed the other two Stynes ​​that Cyrus was there with. Despite begging for his life and claiming that he was different and hated his family, Dean shot Cyrus in the head in cold blood. Of course, this was due to the Mark of Cain, but that doesn’t make him any less villainous.

two Hero – Don’t give up on Sam

Despite everything that happens with siblings, including all the lies and resentment that arise, they are always there for each other. They always protect each other, and Dean sees it as his responsibility in life to take care of little Sammy.

The best example of Dean’s care for Sam comes in “Swan Song”, when he refuses to believe his brother is gone and refuses to give up on him, talking to Sam despite Lucifer beating him to a pulp. bloody. Dean was a catalyst for Sam to take over his body again. Then there are more divisive acts like selling his soul for Sam, stopping him during trials, and making sure Sam goes on in life and is happy without him.

1 Villain – Jack’s Treatment

Jensen Ackles as Dean, Alexander Calvert as Jack, Misha Collins as Castiel, and Jared Padalecki as Sam in Supernatural.

Jack Kline became the fourth member of Team Free Will very late in Supernatural to run. Her relationship with Cas and Sam was constantly filled with love, but her relationship with Dean was incredibly complicated.

Dean literally hated Jack sometimes, and the fandom didn’t like his treatment of Jack. Obviously, he gets close to Jack and treats him well, but Dean was quite abusive towards Jack at times, threatening to kill him and not supporting him emotionally. Between all of that and things like the Jack in the box incident, Dean’s treatment of Jack was far from heroic. He didn’t see Jack; saw Lucifer.

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