Pie is a recurring delicacy favored by Dean Winchester.
The first mention of Dean liking pie appeared in season 1 episode Scarecrow, in which the townsfolk of Burkitsville, Indiana annually sacrifice young couples to a pagan god. The couples are fed pie before their sacrifice. As Dean is held captive and prepared for sacrifice, he exclaims : "I hope your apple pie is freakin' worth it!"
Since then, Dean has made numerous mentions about wanting pie, though a recurring gag is that he rarely ever does get his pie.
In season 5 episode Dark Side of the Moon, it is implied that the origin of Dean's love for pie comes from Mary, who was shown in a memory making him pie. Dean also seems to associate pie with comfort, possibly because of his mother.
After that, Dean is not shown eating pie again, even though pie does appear on numerous occasions. This maybe due to the fact that pie no longer offers him comfort now that he knows what kind of person his mother is, and because of her recent betrayal.
In Season 14's Optimism, Dean gets and eats pie at a diner with Jack while working a case together. Later, in Damaged Goods, Mary brings home pie for Dean while getting supplies for the Winchester Surprise, but he never actually gets to eat it.
In Don't Go In The Woods, pie is apparently on Dean's shopping list for Jack as he is seen examining one. Jack later tells Dean that he bought everything on the list except the beer, as Jack has no valid ID and he didn't want to use a fake one, suggesting that Jack did indeed buy the pie. It is unknown if Dean ever gets to eat it, but it's possible, since Dean had nothing to interrupt him from enjoying the pie after he got back to the Bunker except for going to the store to buy beer.
In Season 15's Our Father, Who Aren't in Heaven, Adam Milligan orders a slice of cake at a diner after returning to Earth from Lucifer's Cage. However, apparently sharing his half-brother's lack of luck with actually getting to eat pie, Adam is interrupted by the appearance of Lilith before he can take a bite. During the following confrontation between Lilith and the archangel Michael, using Adam as his vessel, the cake sits between the two. After Michael obliterates Lilith, the archangel pushes the uneaten cake away from him.
- Season 1
- Scarecrow (first mention)
- Season 2
- Season 3
- Season 4
- Season 5
- Season 7
- Season 8
- Citizen Fang (Dean orders pie at the Guidry's Cajun Café; Martin Creaser is later shown eating pie at the cafe)
- Taxi Driver (Dean buys himself some pie but Kevin Tran takes it)
- Pac-Man Fever (Charlie goes out and promises not to forget the pie; she returns without any pie)
- Clip Show (Castiel fails to buy Dean pie at a convenience store)
- Season 9
- Season 10
- Season 12
- Season 13
- Season 14
- Pie has been shown or mentioned in every season except Season 6 and Season 11.
- In a Season 7 interview, Andrew Dabb noted that he and his now-former partner, Daniel Loflin, wrote many episodes involving Dean's love for pie, such as Dark Side of the Moon, which introduced its origin. Dabb jokingly said that his entire career centered around "pie-writing" because of it.
- When asked in that same interview about the cruelty of Dean not getting any pie in Season 7, Daniel said he was okay with torturing the lead cast, who by default could not be killed off.
- Prior to this, Dean had lost the Impala and Bobby Singer, making the act even crueler.
- Dean and his half-brother Adam Milligan appear to share the same bad luck in never getting to actually eat their favorite baked goods, pie in Dean's case and cake in Adam's.