20 Most Memorable ‘Supernatural’ Adversaries

Since its premiere in October of 2005, Supernatural has been a fan favorite for many viewers. One of the reasons this show has such a loyal fanbase is that they make each season just as exciting as the last.

This is done through the creation of antagonists, who are well worth our time and memory. Taking a look over the long 15-year run, we selected the bad guys that stuck with us after all this time. 

Some of their most memorable adversaries stuck around for only a few episodes, while others have spanned many seasons. Either way, these are not individuals we would want to cross paths with.

It goes without saying that if you haven’t seen all 15 seasons there are bound to be spoilers ahead. In no particular order, we present the 20 Most Memorable Supernatural Adversaries.

1. God

God is arguably the biggest antagonist for the boys considering his reign of chaos begins early on in the series. Technically, we first meet him on Supernatural Season 4 Episode 18, “The Monster at the End of This Book,” when he takes on the persona of Chuck the Prophet.

In fact, he wears the face of Chuck for the rest of the series. However, he’s not as innocent and sweet as Chuck leads us to believe.

Throughout the whole series, God either creates problems or ignores them. He’s constantly preventing the brothers from doing all that they can to make the world a little bit better.

At the end of Season 14, God pulls his biggest move yet and undoes all the good the Winchesters have ever done. Talk about a dick move. This creates chaos for the brothers as they head into the final season.

2. Yellow-Eyed Demon/Azazel

This is the demon who started it all for the brothers. When Sam was six months old, the Yellow-Eyed Demon fed his blood to Sam and then killed their mother.

For the first two seasons the brothers, John Winchester, Bobby, and Ellen, Jo, and Ash hunt the hell out of this demon. It isn’t until the Season 2 finale that Sam and Dean finally vanquish this demon.

However, in that short time, this demon causes the death of Sam’s girlfriend Jess as well as John. His demise is one of the greatest moments of the whole series.

Even though he’s dealt with early on, the effects of his actions affect Sam and Dean for years later. Whether it’s Sam demon presence in his soul or the pain of the losses, this demon is never far from their lives.

3. Lilith

When Dean sells his soul to save Sam’s life at the end of Season 2 his contract goes to a new up-and-coming demon — Lilith.

If we thought Azazel was bad, Lilith makes his chaos look like child’s play. This demon often dons the body of a young girl to throw humans off and make the Winchesters second guess killing her.

Lilith is the demon who took over a whole town and locked the boys in a prison. She also becomes the last seal, which opens the gates of hell and causes all kinds of problems for years to come.

Even now, 15 seasons in there has not been a demon of her caliber since. If Lilith were to somehow come back all hell would break loose — literally. 

4. Crowley

The King of Hell ain’t no slouch when it comes to creating problems in the lives of the Winchesters. He sends his demons after the brothers in the hopes of gaining their souls for himself.

His signature “Hello Boys” always precedes what is bound to be a complicated moment. In the beginning, Crowley refuses to be swayed by anything the Winchesters have to say.

However, over time he bonds with them and is able to be persuaded to help Sam and Dean during moments of major duress with demons and other such dark creatures. He even goes so far as to create nicknames for them — Moose and Squirrel.

Ultimately, Crowley sacrifices his own life for Sam and Dean’s quest of making the world a better place. However, that never takes away from the fact that he has always been a part of the group which they hunted.

5. Lucifer

Throughout the history of TV and film, the fallen archangel, Lucifer, has taken on many forms. And it’s no different on Supernatural.

While his form is mostly that of Nick, he will sometimes take over other vessels. At one point, he resides within Sam and then Castiel. The most entertaining moment for Lucifer is when he’s “haunting” Sam’s mind trying to get Sam to let him in.

One of the only positive things about him is his son, Jack, who joins Team Free Will and considers Cas his father. So you could say that some of the things Lucifer puts them through ultimately help in the end and that is what makes him so much fun to watch.

However, his top personality trait is to terrorize the brothers until he gains what he wants — a ticket back into heaven. In fact, once he’s released from his cage, Lucifer takes over hell in order to gain the upper hand on them, but they never let him win — no matter what.

6. Rowena

Who doesn’t love an all-powerful witch with a Scottish accent? Rowena fits that description to a tee and doesn’t ever let anyone forget it.

She never once picks a side, choosing instead to straddle the line between earth and hell. Her son Crowley may run hell, but she runs him.

Rowena will help the Winchesters but only if it benefits her in the end. After all, Rowena looks out for Rowena and no one else.

She has a strength to her that is unmatched by any other witch or demon combined, which is helpful or harmful depending on where you land with her. That strength is why many fans love her even though she’s a thorn in the Winchesters’ side.

7. Dick Roman/Leviathans

The proof is in the pudding with this guy. Think about it, his name is Dick.

When Dick Roman and the Leviathans come on the scene during Season 7, they initially get the leg up on Dean. After all, he uses his human form and charms to manipulate his way into a position of power to rid the world of demons and gain the ultimate power.

All through Season 7, Sam and Dean struggle to get the drop on this guy. It isn’t until Castiel teams up with Dean and finds a way to vanquish him that the world starts to seem hopeful again.

However, Dick’s demise isn’t without the sacrifice of Bobby for the good of the many. Also, when he’s sent back to purgatory, he manages to pull Dean and Castiel right along with him.

That pull to purgatory teaches Dean and Cas things they still utilize to this day. So in a way, they could say that this experience wasn’t without its payoffs.

8. Abaddon

Just like many adversaries on this list, Abaddon has been around since practically the beginning of time. Her reign of terror against the Winchesters dates back as far as their grandfather in 1958 with the Men of Letters.

She is a lethal killer who takes no prisoners in her quest for souls. Abaddon has one goal in mind — take over both Hell and Earth.

The Winchesters manage to thwart her efforts for a little while by shooting her in the head with a devil’s trap engraved bullet and then cutting her into pieces.

Even though she has been dealt with by the boys, her legacy still remains. Abaddon is a reminder of why they fight for the good of all people.

9. Ruby

Coming to the Winchesters aid during Dean’s year-long quest to get out of his deal, Ruby at first seems better than her demon identity. Her willingness to even try helping is what sets her apart from other low-level demons, even after it becomes apparent that she has ulterior motives.

She is helping Sam and Dean in the hopes they will deal with Lilith and make her life easier, which can we really argue against that?

When Dean gets pulled from hell by Castiel, we soon find out that Ruby is back. The worst part is that she’s gotten Sam addicted to demon blood.

On Supernatural Season 4 Episode 22, “Lucifer Rising,” Ruby reveals herself as a double-agent working with Lilith to free Lucifer. After Lilith is killed, Sam and Dean use Ruby’s own blade to kill her.

10. Death

Considering Sam and Dean have died many times, it’s easy to discern that one of their greatest demons is Death itself. Throughout the seasons, Death appears in many forms.

Death isn’t always after Sam and Dean. Sometimes they are hunting someone else, and the brothers have to attempt to fight off Death. No matter what, Death can’t be defeated — a lesson Sam and Dean take a long time to learn.

During Season 10, Dean is trying to rid himself of the Mark of Cain, so he asks Death to kill him. Death refuses, and so Dean kills him with his own scythe.

This doesn’t mean Death is over and done. Instead, one of his reapers is reincarnated as Death. Through it all, Death is an enemy but also an ally.

11. Gordon Walker

Sometimes the most terrifying enemies aren’t even supernatural in nature. Gordon is one such example — a fellow hunter.

He first comes on the radar of Sam and Dean during Season 2 when they team up with him to hunt some vampires. However, they soon realize he’s a rogue hunter who can’t be trusted.

When Gordon returns in Season 3, he is hell-bent on killing Sam because he believes he’s a monster. This leads to some tense moments between him and the Winchesters and ultimately crosses him with vampires.

Once Gordon is changed into a vampire, it becomes even more dire that he be stopped. Thankfully, on Supernatural Season 3 Episode 7, “Fresh Blood” Sam manages to behead Gordon with a razor-wire garrote.

12. Bela Talbot

Another memorable human foe to the brothers is Bela. This woman is always around the boys throughout Season 3 creating problems for them in her quests to sell off occult items.

She first appears on Supernatural Season 3 Episode 3, “Bad Day at Black Rock.” At this point, she merely steals a rabbit’s foot from the brothers, which coincidentally turns their good luck sour and deadly.

From that moment forward she constantly shows up either as a result of the brothers or in order to attract them to trouble. At one point, in order to avoid legal trouble, she leads the FBI directly to Sam and Dean.

We last see her when she attempts to steal the Colt gun from Sam in an attempt to prevent being dragged to hell. Even though she was nothing but trouble, a part of us is sad she left. 

13. Gabriel/Loki/Trickster

While he is Gabriel the archangel is really helpful to the brothers on their quest to beat God at his own game. However, when he’s posing as a Trickster or Loki, he’s the exact opposite.

We first meet him when he traps the brothers in a Groundhog Day time loop on Supernatural Season 3 Episode 11, “Mystery Spot.” This is how we find out just how deadly his tricks can be.

Gabriel likes to liven up his life by messing around with others. His favorite pawns are the Winchesters, and it shows through the numerous times he shows up and disrupts their lives with petty games.

However, when the chips are down this adversary, much like a few others on the list, would help out Sam and Dean, even if it’s only for a short while.

Ever since his official demise in Season 14, we have missed his easy-going nature in the dismal landscape of God’s treachery. 

14. Raphael

The third of God’s “children,” Raphael is an archangel no one should ever want to cross. He never once strays from his goal of creating the apocalypse which is very admirable and worth respecting.

During Season 4, he protects Chuck from Lilith while creating chaos for Castiel and the brothers. Ultimately, Raphael wants the seals to be broken because it means he’s reached his goal.

While he initially kills Castiel, the angel manages to come back and helps thwart Raphael’s plans for a second time. Raphael continues to create havoc on Earth and refuses to help them find God.

By the time Season 6 rolls around, Raphael has managed to finagle himself back into Heaven. His reign of terror there continues until Castiel manages to kill him once and for all.

15. Meg

Meg, sweet Meg — not! This demon in the body of an innocent girl first manipulated her way into Sam’s life during a Season 1 argument he has with Dean.

Throughout Season 1, Meg is always there to make their lives more difficult and attempt to gain Sam for the Yellow-Eyed Demon. Eventually, she meets her end when the Winchesters exorcise her back to hell, which unfortunately kills the girl she had been possessing.

Meg returns in the body of another innocent young woman during Season 5 as a loyal follower of the recently released Lucifer. She reluctantly joins forces with Sam, Dean, and Castiel for her own plot to defeat Crowley.

Crowley eventually captures her and tortures her for a year. She never once gives up the information he is seeking — instead she gives it to Team Free Will — which earns her a one-way ticket to her demise and a permanent place in our hearts.

17. British Men of Letters

During Season 8 Sam, Dean, and Castiel discover there is a secret society of supernatural threat assessors — the Men of Letters — which Winchester family members were the leaders of. In fact, their grandfather Henry was a famous leader during the final year that the American branch was active.

In Season 11, Sam determines that the members of the British Men of Letters are rogue and need to be taken out. These guys are no joke and ultimately worth a revisit every once in a while just to see Sam and Dean step up to the challenge in big ways.

Sam and Dean go up against these representatives who are much more skilled at hunting than they could ever dream to be. However, the boys’ sheer will and pure luck manage to keep them toe to toe.

On Supernatural Season 12 Episode 22, “Who We Are,” Sam, Dean, Castiel, and Mary pull together a group of American Hunters and launch a full-on assault on the British Men of Letters hunters. They ultimately defeat the Brits and essentially ending their reign of terror in America.

18. Zachariah

One of the many angels who have it out for the Winchester brothers is none other than Zachariah. He isn’t around for very long but his impact is remembered long after.

During Season 4 his main focus is manipulating Sam into releasing Lucifer from his cage. Sam resists his manipulations but it isn’t easy.

Once Lucifer is topside, Zachariah doesn’t just move on to other people. Instead, he doubles down on Dean this time because he needs Michael to kill Lucifer, and Dean needs to become Michael’s vessel.

Zachariah is never far from our minds because he was a fun adversary thanks in part to his devious actions. His power of manipulation was like no other and really put Dean through the wringer. 

19. Uriel

Uriel is introduced as Castiel’s superior during Season 4. He is one hell of an angel and becomes a thorn in the brothers’ side when it is revealed he is a double agent working to restore Lucifer.

For many of the antagonists on this list, it all comes back to Heaven or Hell, which is what makes Uriel particularly memorable as he straddled the line between both.

His betrayal is what ends up leading him to his end. However, it’s not before he comes up against Sam and Dean a few intense times.

Uriel hates humans and thinks they are far beneath him, which is why he turned against God. Unfortunately, he underestimates humans and their ability to help defeat him.

20. Cain

The legend of Cain is well-known and the guy is just as lethal as we could imagine. He is known as the Father of Murder.

His Mark of Cain is just as legendary and the source of all his power. Since he is a direct ancestor of Sam and Dean, his mark is able to be transferred to Dean.

He retires from his murderous ways in the name of love, but Sam and Dean draw him back in to help them defeat Abaddon. By killing her he falls back under the influence of the mark, which leads to his demise.

The influence of Cain is felt for a long time after he is gone due to Dean having his mark. Even after Dean manages to get rid of the mark he feels residual effects for some time. 

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Who are your favorite Supernatural adversaries? Sound off in the comments below.

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Supernatural airs Thursdays at 8/7c on The CW.

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