Every 'Supernatural' Villain's Most Disturbing Moment, Ranked By Pure Evil

List Rules
Vote up the times 'Supernatural' villains did something next-level evil.

Fans generally have their own preferences when it comes to choosing the best Supernatural villains, but the dark fantasy show is such that every antagonist has had at least one moment that truly captures their evil side. Some baddies tend to deal an emotional blow to Sam and Dean Winchester while certain others inflict harm to the boys that is very hard to see.

It's also interesting how their biggest moments of maliciousness capture the villains' characterizations, so Supernatural fans should check out the times when everyone hated the bad guys just as much as the Winchesters. 


  • 1
    412 VOTES

    Chuck Reveals He's Caused All The Tragedies In Sam And Dean's Lives Because It's Fun For Him

    Chuck Reveals He's Caused All The Tragedies In Sam And Dean's Lives Because It's Fun For Him
    Photo: The CW

    Chuck's decisions as God were always very apathetic at best, and the Winchesters noted he never did anything to help anyone. In the 14th season finale, Chuck tries to goad Dean into killing Jack, even handing him a gun that would take Dean's life as well when he successfully shot Jack in revenge for accidentally taking Mary's life.

    When confronted by Sam, who doesn't want Jack to perish, Chuck admits the Winchesters are his favorite form of entertainment, and that he's the one responsible for all the tragedies that have ever happened to them. Chuck reveals that the entire apocalypse scenario and world-ending disasters the Winchesters were forced to deal with were his "stories," and he intends to continue because it's too much fun for him.

    Chuck even has the audacity to be offended when the Winchesters turn on him, claiming he was being nice all along and that they've betrayed him by not complying with his twisted rules. 

    412 votes
  • 2
    359 VOTES

    Lilith Possesses A Child To Torment Her Family Just For Fun

    Lilith Possesses A Child To Torment Her Family Just For Fun
    Photo: The CW

    Lilith knows that the Winchesters will come for her in the third season finale because she holds Dean's contract that will send him to hell. Simply to pass the time, Lilith takes possession of a little girl in a suburban household and proceeds to violently antagonize her family; she calls this her vacation.

    Lilith first kills the family's pet, and then slays the child's babysitter. Lilith then forces the family to act as if nothing is wrong, essentially keeping them in perpetual fear. When the grandfather tries to ask for help, Lilith snaps his neck at the dinner table and coerces the parents to play along so she doesn't end them them in the same manner.

    None of Lilith's violent antics are necessary - she does it just as a way to entertain herself. The family is so scared of the daughter that her mother asks Sam to do away with her, only to learn that Lilith has vacated her body; Lilith wants Sam to take the life of a child for a final taste of sadistic satisfaction.

    359 votes
  • 3
    313 VOTES

    Dick Roman Shoots Bobby In The Head, Taking His Life

    Dick Roman Shoots Bobby In The Head, Taking His Life
    Photo: The CW

    The Leviathan arc in the seventh season is generally considered to be a weaker plot angle for the show, although the main antagonist, Dick Roman, does eliminate the Winchesters' surrogate father for good. The heroes are about to escape from Dick's lair when the villain is hot on their heels. 

    Dick realizes he can't catch his enemies, so he tries to shoot them from afar. As fate would have it, Dick is successful in shooting Bobby in the head, which is so well targeted that there is no hope to save him. Bobby ends up perishing as a result, which leaves the Winchesters with no paternal figure in their lives and turns Dean into a depressed alcoholic.

    When later confronted by Dean over what he did, Dick cruelly arrives outside the hospital where Bobby was admitted to mock his enemy, knowing Dean can't attack him in front of the general public, who thinks Dick is a business magnate.

    313 votes
  • 4
    310 VOTES

    Azazel Forces Mary To Make A Deal For John's Life While Possessing Her Deceased Father

    Azazel Forces Mary To Make A Deal For John's Life While Possessing Her Deceased Father
    Photo: The CW

    Azazel is dead by the events of the fourth season, but he returns when Dean is sent to the past in 1973. It turns out that Azazel had always had a deal to enter the Winchesters' house as he did in the first episode, and that Mary was the one who had given her consent for him to do so.

    As it happens, Azazel first takes the lives of Mary's parents, Samuel and Deanna Campbell, then takes possession of Samuel to attack John Winchester and Mary. Azazel has been told by Lucifer that Mary will give birth to his vessel, Sam, in 1983, so he bargains for John's life in return for entering Mary's house in 10 years. 

    To add insult to injury, Azazel forces Mary to kiss him at a time when he's possessing the deceased body of Mary's father. He could have used plenty of other tactics to get what he wanted, but Azazel chose the most sadistic and disgusting manner for his own sick pleasure that left Mary without her parents and facing certain death in the future.

    310 votes
  • 5
    263 VOTES

    Metatron Causes All The Angels In Heaven To Fall

    Metatron Causes All The Angels In Heaven To Fall
    Photo: The CW

    Metatron holds a grudge against the angels and decides to seek out his revenge by manipulating Castiel. He claims he's assigning Castiel tasks to complete a spell that will seal all angels in heaven so they can live in harmony - but is actually making a spell that will cause all angels to fall.

    Metatron ends up completing his goal, before which he turns Castiel human and casts him to Earth. Castiel is then forced to watch the sky as thousands of angels begin to fall from heaven, which brings everything to the brink of destruction because angels are necessary to hold the balance of heaven in place. 

    Metatron doesn't care about any of the consequences, choosing instead to manipulate the angels once again by painting himself out to be a new god when he's actually drawing power from the angel tablet.

    263 votes
  • 6
    261 VOTES

    Crowley Eliminates Sam And Dean's Friends In Gruesome Ways To Mess With Them

    Crowley Eliminates Sam And Dean's Friends In Gruesome Ways To Mess With Them
    Photo: The CW

    By the climax of the eighth season, Crowley figures out the Winchesters are trying to close the gates of hell due to Crowley's attempts to slay the angels and take over the world. He resorts to petty means by learning about the people the brothers have saved over the years just so he can kill them.

    The people in question have no idea who Crowley is and are completely innocent, but this only amuses Crowley, who terminates them in a variety of ways. Crowley causes one victim's head to explode, cooks a woman in an oven, causes Sam's former love interest to be magically strangled, and nearly makes their mother figure Jody Mills choke on her own blood.

    The Winchesters remind Crowley that their friends aren't involved in their feud, which has no effect on the king of hell, who confesses he finds it fun to eliminate these people in a variety of ways.

    261 votes