Sam (Jared Padalecki) and Dean (Jensen Ackles) have seen their fair share of strange situations over the course of Supernatural‘s wild 15-season run. From vampires targeting Twilight fans to a pagan god masquerading as an heiress, they’ve been through the unthinkable and more while saving people from the evil creatures wreaking havoc in the world.
In Season 13, the show entered weird new territory when it crossed over with the animated classic Scooby-Doo in one of its most mind-boggling episodes to date. “Scoobynatural” was an unforgettable adventure that saw the Winchester brothers transported into a whimsical 2-D world where they joined forces with the iconic Scooby gang to solve a real ghost mystery. As we’ve learned with other out-of-the-box episodes like Season 3’s “Mystery Spot,” which saw Sam trapped in a Groundhog Day scenario in which Dean dies over and over again, and Season 14’s “Mint Condition,” in which the brothers took on action figures brought to life, the series has never been afraid to experiment.
As we approach the end of Sam and Dean’s decade-and-a-half journey, we’re taking a look back at all the Supernatural episodes that made us scratch our heads and wonder, “What the heck did we just watch?” Check out our ranking of the 12 most delightfully bizarre Supernatural episodes ever below.
12. “Last Holiday” (Season 15, Episode 14)
Dean gleefully rocking a periwinkle Ebenezer Scrooge-style nightgown and Sam having his fingernails ripped off by an overprotective wood nymph hell-bent on killing Jack (Alexander Calvert) are just two of the reasons this strange but fun episode made the list. When the Winchesters encounter a magical homemaker who loves to cook and clean, they jump at the chance for normalcy. However, their dream situation of holiday dinners, birthday surprises, and paper bag lunches quickly devolves into a nightmare scenario when their sweet new mother-figure goes full Mommy Dearest — physical torture and all — under the guise of protecting the boys. It’s a friendly reminder that you probably shouldn’t trust the mysterious creature who’s been trapped in your bunker for half a century.
11. “A Very Supernatural Christmas” (Season 3, Episode 8)
In a creepy twist on a festive holiday, the Winchesters investigate the strange disappearances of townsfolk who were snatched up their chimneys by a mysterious creature. While it didn’t exactly ruin Christmas forever, the odd case did make us think twice about waiting for Santa by the fireplace.
10. “Slumber Party” (Season 9, Episode 4)
If you’re still trying to wrap your head around this one, you’re not the only one. Things go off the rails when Sam and Dean find an ancient computer that opens a literal door to the World Wide Web. Inside, Dorothy from The Wizard of Oz has trapped herself and the Wicked Witch in an effort to stop the evil sorceress from using a key that would connect our world to Oz. Yeah, this definitely wasn’t the Oz from your childhood.
9. “Plucky Pennywhistle’s Magical Menagerie” (Season 7, Episode 14)
Clowns are creepy enough on their own. Clowns manifested from your worst nightmare who end up murdering your parents in the middle of the night? Downright terrifying. However, the campy tone makes this episode not so much frightening as just… baffling. But that’s not necessarily a bad thing.
8. “Fallen Idols” (Season 5, Episode 5)
In an episode that can only be described as Hollyweird, Sam and Dean go toe-to-toe with Paris Hilton — err, a pagan god who assumes her identity in order to feed off her adoring fans. While the oddball case doesn’t contain as many twists and turns as we hoped, seeing the hotel heiress wield a giant knife while attempting to devour Sam’s heart is both strange and wildly entertaining.
7. “Mint Condition” (Season 14, Episode 4)
Just when you think you’ve got this crazy little show about demon-hunting brothers pegged, it somehow finds interesting new ways to surprise you. In “Mint Condition,” Sam and Dean battle creepy action figures that are possessed by restless spirits, delivering a boldly fun hour that juxtaposes chilling terror with slapstick comedy. The thrilling story also pays homage to the show’s horror roots with sweet little nods to Route 666 and Hell House, capping off a truly delightful episode.
6. “Changing Channels” (Season 5, Episode 8)
No one has had more fun with the Winchesters than the Trickster (Richard Speight Jr), aka the archangel Gabriel, who messed with the brothers on numerous occasions. This time, he traps them in a series of different television shows. Hanging out in the sleek Grey’s Anatomy-esque medical drama Dr. Sexy, M.D. sounds fun until you realize you could be trapped there forever.
5. “Just My Imagination” (Season 11, Episode 8)
You know you’ve got a doozy on your hands when Sam’s imaginary childhood friend appearing isn’t the strangest part of the hour. This episode centers on a woman seeking revenge for the death of her sister, sparking a murder spree of invisible creatures that forces the Winchesters to take action. Sadly, the Winchesters are too late to save Sparkle, a glittery unicorn man who meets a brutal end when he’s stabbed in the chest with a dagger.
4. “Destiny’s Child” (Season 15, Episode 3)
You think you’ve seen it all, and then Supernatural puts another strange thing into the universe, like spoiled, hipster versions of Sam and Dean who come from an alternate universe in which John Winchester (Jeffrey Dean Morgan) is still alive and they make an absurd amount of money from demon hunting. A lot gets packed into this truly unique hour, which also finds Cas hitting up Ruby (Genevieve Padalecki) in the Big Empty, Jo (Danneel Ackles) revealing that she sells powerful occult items to the highest bidders, and Jack regaining his soul after a trip to Eden.
3. “Mystery Spot” (Season 3, Episode 11)
Dean has kicked the bucket more than a hundred times on Supernatural, and most of those deaths can be attributed to this single episode. In the Trickster’s second appearance, Sam is forced to relive the same day over and over, with the day only restarting after Dean’s unfortunate passing due to some truly creative means, including getting a piano dropped on him and eating bad tacos.
2. “The French Mistake” (Season 6, Episode 15)
Sam and Dean are no strangers to alternate worlds, but this one — in which they’re actors known as Jared Padalecki and Jensen Ackles on a TV show called Supernatural — is truly bizarre in the best way possible. Featuring callbacks to the stars’ real lives and several scenes that blur the lines between fiction and reality, this meta episode stands as one of the show’s most unforgettable installments to date.
1. “Scoobynatural” (Season 13 Episode 16)
The boys get animated in what will go down as Supernatural‘s most ambitious episode ever. When an old TV transports Sam and Dean into the world of Scooby-Doo, we’re met with a fun-filled mystery for the ages. Positioning our beloved demon hunters alongside the wholesome Scooby gang could have been a tonal misfire, but Supernatural perfectly blends its unique sense of humor with Scooby‘s classic hijinks, proving that Supernatural has only getting better, and weirder, with age.
Supernatural‘s series finale airs Thursday, Nov. 19 at 9/8c on The CW. An hour-long retrospective, Supernatural: The Long Road Home, will air prior at 8/7c.
In honor of Supernatural coming to an end after 15 seasons, TV Guide presents Winchester Week, a celebration of Sam, Dean, and the entire SPN Family. Find out how the stars feel about saying goodbye, look back on the best episodes and moments, and join us in sending the Winchesters off in style.