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Destiel vs. Wincest: A History Of Supernatural's Craziest Ships

Updated November 6, 2020 13.0k votes 1.8k voters 19.5k views14 items

List RulesVote up Supernatural's most bizarre ships.


Supernatural has always been a show that’s very aware of its fanbase and what its shipping preferences are. In fact, the show has made references to these ships on more than one occasion. The show is incredibly meta (that's part of its appeal), and has mocked (while also celebrating) its fandom through a popular book series that exists within the show -- a series called Supernatural. It's pretty on-the-nose. The fans of the novels within the show ship Wincest and Destiel with as much zeal as their real-life counterparts.

Some of these ships pair angels with angels, some angels with demons, and some humans with classic cars. If that’s the type of thing that ruffles your celestial feathers, it’s best you turn back. If that type of thing revs your engine, then carry on my wayward son. (Insert epic drum noises). 


  • 5

    Team Free Will

    Photo: CW

    Characters: Dean Winchester, Sam Winchester, and Castiel

    The more the merrier, right? This ship combines the two biggest pairings in the fandom, Destiel and Wincest. The name “Team Free Will” was coined by Dean himself who described Sam, Castiel, and himself as "one ex-blood junkie, one drop-out with 6 bucks to his name, and Mr. Comatose over there." Whether they’re taking on the apocalypse, Leviathans, Lucifer, or Crowley, it’s the ship that never quits. There's probably a sailing joke in there somewhere, but whatever. 

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  • 6


    Photo: CW

    Characters: Charlie Bradbury and Jo Harvelle

    One of the most fun things about shipping fandom is the ability of fans to rationalize the shipping of two characters who have never met. Charvelle often appears as a secondary pairing in Destiel fanfiction. As two badass female hunters, they would have been a force to be reckoned with. Too bad they’re both dead, like pretty much every major character on Supernatural. Still, it's fun to dream. 

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  • 7

    Sam And Jess

    Photo: CW

    Characters: Sam Winchester and Jessica Moore

    Even though the demon Azazel manipulated Sam and Jess into falling for one another, their love was as sweet and as wholesome as Supernatural gets. Sam’s world was a different (arguably better) place when he was with Jess. He was bound for law school, he hadn’t seen his brother Dean in a while, and he was planning on proposing to the girl he loved. Though the show has paired Sam with several women since Jess, she still holds a special place in Sam’s heart. 

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  • 8


    Photo: CW

    Characters: Sam Winchester and Lucifer

    This is one of the unhealthier ships out there (since the pairing would be non-consensual), but there is a group of fans who ship Sam and Lucifer. Much of Lucifer and Sam’s dialogue sounds vaguely flirtatious. Lucifer would often promise Sam happiness, like in the following quote: “I wanna give you a gift. I wanna give you everything.” It should be noted that Lucifer has appeared to Sam in many forms -- as Jess, as Cas, as his original vessel, and as a version of Sam himself, so fans of the pairing have a lot to work with, imagination wise.

    Is this bizarre?