VOICE OVER: Rebecca Brayton WRITTEN BY: Saim Cheeda
The most entertaining demons on "Supernatural" made being bad look so good. For this list, we'll be looking at those demons in this dark fantasy series that not only excel as villains, but also have enough charm to make fans follow them for their entertainment value. Our countdown includes Ruby, Cain, Dagon, and more!

Top 10 Most Entertaining Demons on Supernatural

Being bad has never looked this good. Welcome to MsMojo, and today we’ll be counting down our picks for the Top 10 Most Entertaining Demons on Supernatural.

For this list, we’ll be looking at those demons in this dark fantasy series that not only excel as villains, but also have enough charm to make fans follow them for their entertainment value. These include their onscreen presence, effectiveness in storytelling, and how memorable they are.

#10: Belphegor

At the heels of Jack’s death, this demon makes his presence known by possessing Jack’s body. Unlike the sinister attitude that demons usually exhibit, Belphegor comes across like an ascended fanboy who’s just glad to be there. He instantly brings in a sarcastic energy to proceedings, which is a welcome attitude considering the predicament the heroes have been left in by Chuck. Castiel’s suspicions with Belphegor also provide an interesting dynamic as his intentions are kept a mystery. Mainly, it’s Belphegor’s ability to simply roll with how things are going that make him so engaging, as he always has something funny to say no matter the situation. The reveal of his evil plans and subsequent death are disappointing, but Belphegor does manage to stay alive in memory.

#9: Ruby

Season 3 sees the arrival of Ruby, a demon who backs up her claims by displaying her badass qualities. It’s in her first vessel where Ruby delivers the most memorable moments, as her no-nonsense demeanor makes her instantly intriguing. Due to her knack for showing up and saving the heroes just in time, Ruby is established as a force to be reckoned with. Her occasional sarcasm also makes her something of an audience surrogate, as she conveys to the Winchesters what the viewer’s probably thinking. Her personality in the fourth season is much less spectacular. However, Ruby’s manipulation of Sam, and the eventual reveal of her betrayal, are plot points that Supernatural fans begrudgingly admire her for pulling off so well.

#8: Meg Masters

If there’s a demon who’s gone through significant character development, it has to be Meg. Starting off as the first real villain for the Winchesters to fight, this unnamed demon who takes on her first host’s name - Meg Masters - eventually turns into one of their allies. Still, Meg’s responsible for introducing moments of horror to the show, and her constant antagonism of the boys serves as one of the overarching premises of the first season. In her initial appearances, Meg shows up when least expected, usually providing an intense conflict into the story. All things considered, the most entertaining aspect about Meg has to be her relationship with Castiel when she’s in her later vessel. Making for a real “opposites attract” situation, her dynamic with her “Clarence” turns out to be both hilarious and heartwarming. Not to mention how Meg always has a quip in handy to annoy her enemies.

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#7: Cain

It’s hard to find any character in Supernatural who’s nearly as cool as Cain. As the first Knight of Hell, his powers are incredible to behold, and the manner in which he uses them is certainly worthy of highlight reels. Despite only a handful of appearances, Cain made an impact instantly. From his tortured history of love and loss, to his struggles with the Mark, there’s a highly intriguing backstory to follow with Cain. Due to his quiet demeanor, any action taken on his part is guaranteed to have an impact. Even his fatal clash with Dean, under the corruptive influence of the Mark, is an intense scene that sums up the inner turmoil of the character.

#6: Abaddon

Thriving on the sadistic pleasure she receives from bringing harm to her victims, Abaddon represents the classic demon archetype. After the later seasons of Supernatural made demons relatively weak, Abaddon’s arrival as a sheer force is a breath of fresh air. Her dark humor not only serves as a perfect way to heighten the tension, but also elevates the story as Sam and Dean’s mission to hunt her down is brought into focus. Her total lack of empathy sets Abaddon up to be a villain who’s meant to be hated by the viewer, although it’s difficult not to marvel at her more powerful moments. Her simultaneous conflict with Crowley provides an additional layer to her characterization, making Abaddon the demon queen not to be trifled with.

#5: Dagon

Unlike most demons, who lack proven feats, Dagon displays most of the devastating potential of these antagonists. Showing up as Lucifer’s most powerful general as a Prince of Hell, Dagon leaves a path of destruction in her wake. The enjoyment she clearly derives from her position comes across as an impressive part of her character, as Dagon is more than content with belittling her victims before finishing them off. Her attempts at keeping up with contemporary lingo are even more hilarious considering her advanced age, although Dagon does pull it off well. Due to the quick succession with which she carries out Lucifer’s plans, showing off her incredible powers in the process, Dagon brings some much-needed energy into the series.

#4: Lilith

As the first demon ever created, it’s natural that Lilith would be the least merciful. Her characterization varies on the vessel she inhabits, being at her scariest when possessing little girls. In season 3, the delights she experiences in torturing an innocent family by using the body of their daughter establish Lilith as the horrific antagonist she is. This represents the highest quality in horror Supernatural can deliver, and Lilith more than brings this genuinely scary feel forward. The mystique around Lilith is furthered in an adult vessel, as she takes upon a calculating attitude that makes it impossible to predict her next move. Upon her resurrection by Chuck in Season 15, Lilith also develops a twisted sense of humor, bringing further personality traits to her character.

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#3: Alastair

Every demon has shown a fear of angels and the concept of death, all except Alastair. Known as the Grand Torturer of Hell, this white-eyed demon is easily the most vicious of his kind. No matter which body he possesses, Alastair’s taste for pain is evident and he makes no effort in hiding it. Due to his role as Dean’s torturer in Hell, Alastair is one of the very few characters who can get under Dean’s skin. This makes their interactions both visually and intellectually stimulating, as the two try to get the other to break. Alastair’s mannerisms, resembling those of Marlon Brando, allows him to dominate any scene the moment he enters. Alastair’s complete defiance, even in the face of death, cements his place as a villain one can’t help but respect.

#2: Azazel

In many ways, it’s Azazel who should be credited with making Supernatural the success it is. As the first Big Bad of the series, it’s Azazel’s mixture of conniving nature and demonic powers that establishes the series’ fantasy horror premise. Every move Yellow Eyes makes has a certain style, whether it’s his ability to drive fear in the hearts of the Winchesters, or antagonize anyone else. The aura around Azazel is such that even his absence elevates his reputation, making each of his appearances a terrifying reveal. From his killing of Mary, to sending John to Hell, Azazel’s actions have an enormous impact on the brothers. It’s due to this personal vendetta that Azazel remains so engaging. Not to mention the one-liners that he makes sure to drop.

Before we unveil our top pick, here are a few honorable mentions.

Asmodeus
Because This Demon Sure Can Rock a Suit

Ramiel
Because This Demon Can Pack a Mean Punch

Seven Deadly Sins
Because These Beings Prove Why Demons Belong in Hell

Demon Dean
Because This Winchester Thrives in His Malevolence

#1: Crowley

While he’s not the most powerful, only becoming a demon after the death of human Fergus MacLeod, Crowley has taken down the biggest and the baddest in the supernatural world. With his highly cunning mind, the once King of the Crossroads easily manipulates anyone around him. It’s not a usual occurrence to see him lose his cool, as the charming and collected King of Hell can easily charm his way out of any situation. With his knack for making jokes at the expense of others, Crowley employs his snarkiness to gain control. His fleshed out backstory allows for Crowley to have long-lasting dynamics with each main character, and it’s always a joy to see how Crowley unsettles them using his trademark humor. Also excelling as a villain, his ability to tap into his darker side makes him just as dangerous as he is entertaining.