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Dean savors some pie in 5.15 Dead Men Don't Wear Plaid

Pie entered the Supernatural idiom in 1.11 Scarecrow, where the townsfolk of Burkitsville, Indiana annually sacrifice young couples to a pagan god who resides in a sacred apple tree. The couple are fed pie before their sacrifice. As Dean is held captive and prepared for sacrifice, Dean exclaims: "I hope your apple pie is freakin’ worth it!"

After 1.11 Scarecrow it became widespread fanon that Dean loves pie - long before he fatefully asked Sam to get him some at the beginning of 2.21 All Hell Breaks Loose: Part One:

Dean: Hey, see if they've got any pie. Bring me some pie. I love me some pie.

In her Ten Expressions Picspam for that episode, kroki_refur told an alternate version of the episode, where Sam did not die but rather Fell on pie.

Where's the pie?

The running gag relating to Dean's pie love, is that Dean rarely gets to eat his pie.

  • 1.11 Scarecrow In Burkitsville Indiana Scotty's Cafe serves apple pie made from the towns apple crop. "We’re famous for our apples. So, you gotta try this pie." he tells a couple who the townsfolk will later try to kill. Dean orders a piece of the pie. Later when Dean is tied up as a sacrifice, he yells the now classic line ""I hope your apple pie is freakin’ worth it!"
  • 3.05 Bedtime Stories: when a young couple, Ken and Julie, are lost in the woods, they come across a sweet old lady who invites them inside her house to rest. Ken sees pie cooling on her windowsill and accepts her invitation despite Julie's reservations. Once they've eaten a fair amount of the pie, it is revealed the pie was poisoned, and the old lady kills Ken with a butcher's knife while he lies on the floor unable to fight her off.
  • 3.16 No Rest for the Wicked: when Lilith kills her host's grandfather, he literally falls face first onto a piece of pie. Some fans believe this to be a shout-out to kroki_refur's aforementioned picspam.
  • 4.01 Lazarus Rising: when Sam and Dean are in a diner following Dean's resurrection, Dean orders pie. Unfortunately, the pie is brought to them by a possessed waitress, and Dean is unable to enjoy it. After their confrontation with the demons in the diner, Dean leaves money to pay for the pie.
  • 5.16 Dark Side of the Moon: In Heaven, Dean and Sam relive a memory from when Dean was four years old. Mary makes him a sandwich with a glass of milk and then has a brief argument on the phone with John. Dean goes to comfort her, and Mary hugs him and says "You are my little angel. How ‘bout some pie?" This may be a clue to the origin of Dean's love of pie, and his associations between pie and comfort.
  • 5.19 Hammer of the Gods: Mercury tells Dean after checking in that the hotel has "the best pie in the tri-state area." Sam also warns Dean that they should leave the motel while eating at the buffet:
Sam: We should hit the road, Dean.
Dean: In this storm? What, it’s, it’s–
Sam: It’s Biblical, exactly. It’s friggin’ Noah’s ark out there and we’re eating pie.
  • 6.04 Weekend at Bobby's: Bobby's neighbor Marcy Ward brings him a ginger peach cobbler. Marcy, after some exposure to Bobby hunting, decides against dating Bobby, who never gets to eat the pie because he keeps getting interrupted.
  • 7.03 The Girl Next Door: While laid up with his broken leg, Dean asks Sam to go on a food run. When Dean asks, "Where's the pie?" Sam says, "You got cake, that's close enough, right?" Dean does not eat the piece of cake.
  • 7.05 Shut Up, Dr. Phil: Dean is in the motel room, about to eat a cream pie, when Sam comes in and presents him with some chickens feet that they require to combat the Witches. They have not been refrigerated due to a power blackout, and Dean is put off his pie.
  • 7.22 There Will Be Blood: Dean is devastated to learn that the modified corn syrup the leviathan are using to make humans docile and obese is in nearly all his favorite foods, including pie.
  • 8.09 Citizen Fang: At the Gumbo Shack, Dean asks Elizabeth for some pie, but she is out of what he wants. "You’re out of pecan? Story of my life," says Dean.
  • 8.20 Pac-Man Fever: Charlie Bradbury comments: "I will pick us up some grub, and unlike you Sam, I will not forget the pie" referring to Sam's long history of failing to get Dean his Pie as requested, a fact she obviously read in the The Supernatural Books. Notably, Charlie also fails to get Dean any pie.
  • 8.22 Clip Show: At the Convenience store, Castiel buys things he knows Dean likes: beef jerky, beer, a copy of Busty Asian Beauties, toilet paper. He tries to buy Pie, but of course to no avail, continuing the running gag in which Dean never gets his pie.

Sam: Look at these chemicals. Do you even read the label?
Dean: No. I read "pie." The rest is just "blah, blah, blah."

It does not appear that Dean gets a chance to eat the pie.

Pie as metaphor

In the 1.01 Pilot when Dean confronts Sam about running away from the way they were raised, he accuses Sam of wanting an "apple-pie life." As opposed to the hunting life, an apple-pie life seems to be the ideal, normal American existence. The phrase "apple-pie life" and even just "apple pie" itself is used in later episodes to refer to normality.

  • 4.22 Lucifer Rising: when it seems like Dean has given up on Sam, Bobby gives him a talking to.
Bobby: Are you under the impression that family's supposed to make you feel good?! Make you an apple pie, maybe? They're supposed to make you miserable! That's why they're family!
  • 5.12 Swap Meat: when Sam is returned to his own body, he confides in Dean that life as a normal kid "sucked ass."
Sam: All that apple-pie, family crap? It's stressful. Trust me, we didn't miss a damn thing.
  • 5.22 Swan Song: when Sam is preparing to say yes to Lucifer, he makes Dean promise that he won't try to get him back from Lucifer's Cage. He wants Dean to find Lisa and try to live a "normal, apple-pie life."
Dean: You say you're "just folks," yeah? That - that you like baseball and apple pie, or whatever. But truth is, I don't know what you are, 'cause you're not Sam.
  • 6.11 Appointment in Samarra: Death tells Dean "What do you think the soul is? Some pie you can slice? The soul can be blundgeoned, tortured, but never broken, not even by me."

Pie and Sex

"Eating pie" is a euphemism for cunnilingus, so it's probably appropriate that Dean loves pie. A lot. source

Sweet Cherry Pie

The song "Cherry Pie" by Warrant is referenced twice:

Sam: It's more of a beautiful creature that preys on men. Entices them with their siren song.
Dean: Let me guess. "Welcome To the Jungle." No, no... Warrant's "Cherry Pie."
  • 5.13 The Song Remains the Same: The song plays during Dean's dream. Two strippers, one dressed as an angel and one dressed as a demon, give him a private dance to the lyrics:
She's my cherry pie
Cool drink of water
Such a sweet surprise
Tastes so good
Make a grown man cry
Sweet cherry pie, oh yeah
She's my cherry pie
Put a smile on your face
Ten miles wide
Looks so good
Bring a tear to your eye
Sweet cherry pie

Pie as Harbinger Speculation

It's okay; Sam just Fell on pie.

Throughout the course of the series, the appearance of or reference to pies appears to foreshadow some threat or danger. This is similar to the use of oranges in The Godfather movies. In almost every episode where pie is shown or referenced, a character or several characters die. Of course this could be said of nearly every Supernatural episode!

The relationship of 4.01 Lazarus Rising and 5.15 Dead Men Don't Wear Plaid to the theory is somewhat unusual. In the former, while the demons are a threat, and are dispatched, the pie might also reference the greater and more serious 'threat' revealed in the episode: angels. In the latter, most of the people destroyed in the episode are already zombies. However, it can be debated either way: the zombies in the town, including Bobby's wife who was making the pies, are already dead and had to be killed again. And at least three humans did die in the course of the episode. It is also possible that the large number of pies foreshadow the appearance of Death, the Horseman of the Apocalypse. It is revealed at the end of the episode that Death raised the zombies. Later, in 5.21 Two Minutes to Midnight, it is discovered that Death likes Chicago pizza, which is sometimes referred to as 'pie'.

It could be argued that there is always some danger around the Winchesters, and the pie theory is not infallible - plenty of characters have died in Supernatural - some several times (i.e. Dean in 3.11 Mystery Spot) - without any reference to or appearance of pie.