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The 14 scariest 'Supernatural' episodes you should watch for Halloween

Sam and Dean Winchester have racked up a lot of mileage saving people and hunting things. Just in time for October 31, here are their scariest road trips.

By Phil Pirrello

Supernatural has survived a change in networks and 15 years of ever-evolving television business models to become one of the most iconic and essential genre shows ever made. 

The simplistic premise is so good, its loyal legion of fans wishes they came up with it: Two brothers-turned-paranormal hunters — Sam (Jared Padalecki) and Dean Winchester (Jensen Ackles) — struggle to stop supernatural threats from pushing into our world. With their foot on the gas of a black '67 Chevy Impala (and a trunk full of weapons and firepower), Sam and Dean traverse the United States like a shotgun-wielding, leather jacket-wearing Mulder and Scully. Instead of UFOs and conspiracy theories, though, Sam and Dean hunt demons, vampires, shapeshifters, and (gulp) clowns. In doing so, Supernatural has evolved from weekly “Monster of the Week” entertainment to a compelling, dense saga that puts the brothers in the middle of a literal battle between heaven and hell, angels and demons, and with a Costco-sized amount of jump scares and terrifying moments in between. 

As Halloween creeps up on us this year, we’ve put together the 15 scariest Supernatural episodes (in order of release) that you should watch or revisit before Oct. 31. 

1. 'Pilot' (Season 1)

15 years after it aired, Supernatural’s debut episode is still effectively chilling, thanks to its Urban Legend-y horror tone and that shocker ending where a helpless Sam watches his girlfriend suffer the same fate as his mother: Pinned to a ceiling while burning alive. 

The Brothers Winchester’s first “Freak-of-the-week” mission kicks off with the night terrors-inducing “Woman in White,” who kills all those who offer to give her a ride. As a villain, she provides the perfect vessel for the show to establish both the dynamic between estranged brothers Sam and Dean and the show’s old-school approach to horror. Shooting on film lends the hour a gritty, Tobe Hooper feel that would carry through the entire first season. As successful as the episode is in the scary department, it’s even more effective at grounding all the frights on the backs of characters you can’t help but invest in — thanks to the tragic tale of how they lost their mom and how that loss impacted their Hunter father, John (Jeffrey Dean Morgan).

2. 'Bloody Mary' (Season 1, Episode 5)

“Bloody Mary” marks when Supernatural hit its stride; a perfect template for what audiences can expect week in and week out. 

This episode brings the urban legend of Bloody Mary to life, as teenagers conjure her vengeful spirit by saying her name three times into a mirror. Sam and Dean struggle at first to grasp the severity of their latest hunt, given Mary’s history of being nothing more than a dare kids engage in at sleepovers. But they quickly realize Mary is very real and a victim herself: At 19, she was murdered before a mirror with her eyes surgically removed (gross). She died before she was able to scrawl her killer's name onto the mirror, and has been dishing out revenge ever since.

Each of her victims is guilty for causing the death of an innocent, and that's when Supernatural ratchets up the creep factor when she targets Sam next. The boys corner her in an antique shop, and force the vengeful entity into a rage that almost costs Sam and Dean their eyes.

3. 'Skin' (Season 1, Episode 6)

Typical procedurals involving serial killers are already scary. Bring in a shape-shifting element so the murderer can take on other forms (including Dean)? Doubly terrifying.

“Skin” is an underrated episode from the first season, one that milks the show’s slow-burn tension for all its worth as it finds inventive ways to make the genre-staple threat of a shapeshifter fresh and scary again. Its most frightening scene is also one of the show's most iconic, when the shapeshifter tears and sheds its skin into bloody clumps.

4. 'Asylum' (Season 1, Episode 10)

"Asylum" is a clever, frightening "bottle episode" that achieves Blumhouse-level scares as Sam and Dean take on a condemned mental institution and the violent spirits within. 

This Season 1 episode finds ways to liven up that tried-and-true concept by confining Sam and Dean to one of the most goosebump-y locations they have ever encountered, complete with ghosts that are just as insane now as they were when they were alive. The creepy set design and lighting scheme make “Asylum” a non-stop delivery system of haunting images as the Winchesters grapple with one of their darkest cases ever.

5. 'Scarecrow' (Season 1, Episode 11)

"Scarecrow" reminds us why road trips through small towns never end well.

Supernatural’s take on the horror movie Jeepers Creepers, with young couples being sacrificed by rural locals in order to appese their pagan god that takes on the form of the titular figure. Sam and Dean's attempts to stop this malevolent deity force them to endure one too many nights in a haunted apple orchard that the scarecrow turns into a twisted killing ground. The sight of the baddie getting down off his pole before getting his murder on will forever give us the creeps, as will the way the townsfolk get a taste of their own medicine when their golem turns on them. 

6. 'The Benders' (Season 1, Episode 15)

Submitting Dean to intense and disturbing levels of torture is a popular trope on the show, and it arguably reached its highest (er, darkest) point in “The Benders.”

The twist here is that the threat the brothers face isn’t a monster from Hell, but rather hillbilly cannibals — which proves to be much worse. What the cannibals are capable of would make the usual Supernatural demons and ghouls blush, as they hunt and trap human game for their own sadistic enjoyment. The back half of the episode contains some of the most riveting and intense sequences in the entire series, as Dean's attempt to save Sam from captivity gets him captured and beaten by the murderous family. 

7. 'Everybody Loves a Clown' (Season 2, Episode 2)

The infamous clown episode. *Shudder*

Still reeling from the recent death of their father John, Sam and Dean are searching for answers (and maybe a little vengeance) as they search for John’s killer, the Yellow-Eyed Demon. All of that leads to a case involving a circus that is home to a clown that stalks children before preying upon their parents. 

Loosely inspired by Stephen King’s novel, IT, “Everybody Loves a Clown” matches that chilling novel in the constant scares department. Especially when Sam and Dean uncover the clown's Hindu-based origins and who in the circus is behind the clown's efforts to snack on human beings. Fifteen years later, this unnerving episode still holds up. 

8. 'No Exit' (Season 2, Episode 6)

Dean and Sam grapple with the ghost of H.H. Holmes, the world’s first serial killer ever, as he resumes his crime spree. His targets? Young girls who resemble the novice Hunter, Jo. She joins the boys for this ectoplasm-heavy case, one that alternates between scary and rocking-back-and-forth-in-the-shower horrifying.

In addition to bodies, the deprived and angry killer leaves behind black slime as Sam and Dean race against the clock before the killer turns Jo into his next victim. The scariest moments are when Holmes drags Jo down into the sewer and puts her inside a coffin. "No Exit" balances the terror with a strong emotional storyline, as Jo and the Winchesters see the toll it takes to dedicate your life to stopping things hellbent on taking that life away from you. 

9. 'Playthings' (Season 2, Episode 11)

One of the few things more disturbing than murder-powered clowns are creepy, murder-powered dolls. Even Jensen Ackles has admitted this Season 2 classic still scares the sh** out of him — and for good reason.

Possessed porcelain dolls pull an R-rated Toy Story when Sam and Dean pay them a visit at the very old and haunted inn they call home. Susan runs the joint and lives there seemingly with her two little girls. But things go from zero to "can’t-stop-screaming" when the brothers realize that only one of the little girls on the premises is human. The other is a spirit that has taken the form of an imaginary friend that has redrum on her mind. The tragedy behind why this “imaginary friend” haunts this place, and how the Winchesters stop it, will leave you wishing you watched this episode with the lights on. 

10. 'Roadkill' (Season 2, Episode 16)

Battlestar Galactica’s Tricia Helfer guest stars as a wife searching for her missing husband following an accident on haunted Highway 41 in Nevada. Similar to the “Woman In White” from the pilot, this stretch of road is haunted by Jonah Greely who, 15 years ago, was hit by a car and left for dead.

Now, he stalks the living in search of someone to punish for his fate. The clever twists this ghost story/slasher film hybrid takes are among some of the best ever in a Supernatural script, bolstered by the tragic, sad mythos surrounding the case and that shocker ending.

11. 'The Kids Are Alright' (Season 3, Episode 2)

Changelings that can mimic any child’s likeness it encounters is the type of horror plotline that would make Wes Craven and John Carpenter jumpy. Leave it to Supernatural to find a way to ground this creepy premise with a verisimilitude that will have you looking over your shoulder the whole time you’re watching.

Instead of just one creepy child, “The Kids Are Alright” is besieged by a town full of them. And who is to blame for this fresh hell? Dean, when he decides to visit an old flame who calls this evil place home for both her and her son, Ben. And yup, Ben is basically mini-Dean, and seeing himself in her boy bubbles up all sorts of father-son issues Dean had with his own dad. As if a changeling that kills fathers and eats mothers wasn’t challenging enough of a project, Dean has to also confront his daddy issues in an episode that has some of the series’ most frightening images ever.

12. 'No Rest for the Wicked' (Season 3, Episode 16)

You know what the problem is when you make a pact with a crossroads demon? The demon always comes to collect.

Dean learns this lesson the hard way when the one-year lease on his life is up and he has 30 hours left to live in the epic Season 3 finale. One of the series’ most popular (and infamous) villains, Lilith, holds the contract on Dean’s soul and Sam struggles to find any loophole to save his brother’s life. But he can’t. He doesn’t. So Dean dies.

While both Dean and Sam have died and been resurrected before, a lot, on the show, this was the first and it’s the scariest. All hope is lost when hellhounds rip Dean apart and drag him down to Satan’s lair, leaving us with the sad, horrible sight of a tortured Dean screaming his brother’s name as Hell burns around him.

13. 'Soul Survivor' (Season 10, Episode 3)

Supernatural quickly burned through its “Freak of the Week” storylines early in the first third of its lifespan, but it still managed to pack in legit scares in later seasons and find new ways to deliver them. 

“Soul Survivor” is Supernatural’s take on The Shining, as a possessed Dean goes full Jack Torrance on Sam when the latter is hiding in a bunker trying to find a way to save his brother without killing him. Dean is straight-up terrifying with his black demon eyes as “redrum” is all he wants. But, in one of the most unforgettable shots of the series, Dean’s attack on Sam is held off with help of angel Castiel (Misha Collins). Again, the reason why fans have been invested for nearly two decades is because of the characters and “Soul Survivor” rewards that time well spent with this heartfelt beat among these characters that serve as the show’s beating heart.  

14. 'Dark Dynasty' (Season 10, Episode 21)

Supernatural is a virtual conveyor belt of disturbing threats and villains to keep the boys on the hunt and at work. And in “Dark Dynasty,” we see that business is booming when the terrifying Styne Brothers come calling. 

The Stynes want the Book of the Damned, a dangerous MacGuffin they believe is in the possession of one of the show’s most popular recurring characters, Charlie (Felicia Day). While this episode doesn’t mainline horror the way early hours in the series’ run did, it does achieve the same level of terror in short bursts. Particularly when Charlie gets bested by the Stynes and our main characters suffer one of the show’s biggest gut-punch moments. Sam and Dean, guns drawn, enter the ravaged hotel room and follow a bloody trail to the bathtub. Where, after holding onto their grimaces for several beats too long, we see what they wish they didn’t: Charlie, a bloody mess, dead in the bathtub. 

She gave her life to save Dean and Sam, and that sacrifice breaks Dean. It sparks Dean to go all “Man on Fire,” with a vendetta that won’t end until he catches up with the Stynes. It’s a dark, but necessary, turn for the character that makes him almost scarier than the things he has spent a lifetime hunting.