Ranking the Best Alternate Versions of Sam and Dean Winchester on ‘Supernatural’

Chris King
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Supernatural ended Season 13 with a major twist as Dean opened himself up to be a vessel for the Apocalypse World’s Michael in order to kill Lucifer and save Sam and Jack. Dean’s decision was nearly a decade in the making; he has known he was the Michael Sword since Supernatural Season 5, but up until the Season 13 finale, he had never allowed the archangel to possess him.

Desperate and determined to protect his family, Dean finally agreed to let Michael take control, which has set up a familiar but exciting direction for Supernatural Season 14. Viewers will get to watch another alternate version of a Winchester brother, a fun trope that the series has used numerous times throughout the years.

With Michael Dean expected to play a major role in Supernatural Season 14, we’re counting down the top alternate versions of Sam and Dean Winchester from the show’s first 13 seasons. From worst to best, here are our picks.

8. Dean Smith

“It’s A Terrible Life” is a pivotal episode of Supernatural Season 4. Zachariah sticks Dean in an alternate world in which he and Sam aren’t brothers or hunters. Instead, they work in the same office building without ever knowing each other. It’s all done to prove to Dean that he can’t turn away from his life as a hunter and that he needs to accept the terrible things that happened in Hell and move forward.

But it also gives us Dean Smith, our most boring version of Dean Winchester. He’s a suit-wearing businessman who drives a Prius and listens to NPR. Need I say more?

7. Sam Wesson

Viewers can also find the least interesting alt-version of Sam in “It’s A Terrible Life.” As Sam Wesson, Sam sits in a cubicle all day, answering the phone and helping customers repair their broken computers.

The one wrinkle about this version of Sam in this episode that makes him slightly more interesting than Dean is that he has dreams about hunting. Also, I do love that the brothers’ alternate last names come together to form “Smith & Wesson.”

6. Dog Dean

A dog does not actually possess Dean during the Season 9 episode “Dog Dean Afternoon.” However, a spell does allow him to communicate with other animals and exhibit dog-like traits, so it’s essentially as if a dog is in control of Dean Winchester’s body for a whole hour of the series.

Is “Dog Dean Afternoon” one of the best episodes of Supernatural ever? Not at all. It’s definitely one of the show’s cheesier installments, but it also features plenty of stupidly hilarious moments, including Dean getting knighted as an “honorary dog.”

5. Gadreel Sam

Gadreel Sam is, in a lot of ways, just as dull as computer fixer Sam Wesson, but he’s also an incredibly important character as well. Gadreel is vital to the main story arc of Supernatural Season 9.

Gadreel begins the season impersonating the angel “Ezekiel,” which is why Dean initially trusts him, but once he reveals his true self, he’s one of the major antagonists for most of Season 9. Gadreel remains a thorn in the Winchesters’ side until he sacrifices himself to save Castiel and hopefully take down Metatron in the Season 9 finale. This action redeems his character and proves why he deserves to be ranked higher than Sam Wesson.

4. Future Dean

Future Dean from the post-apocalyptic world of the Season 5 episode, “The End,” has none of the goofy humor of Dog Dean. This version of Dean is the most ruthless and most broken version of him we’ve ever seen because he lives in a future in which Sam has willingly said “Yes” to being Lucifer’s vessel.

“The End” is one of my personal favorite episodes of Supernatural. Future Dean is compelling because he serves as a reflection of all of Dean’s worst impulses, the type of man he could so easily turn into if he didn’t have Sam with him to help guide him. It’s a reminder to Dean as a character and us as viewers just how important the bond between the brothers is. Also, Jensen Ackles delivers an absolute powerhouse performance as the character.

3. Lucifer Sam

Lucifer Sam, in both “The End” and in “Swan Song,” is violent, cruel, and merciless. He snaps Bobby’s neck with a flick of his wrist, causes Cas to explode with the snap of his fingers, and beats Dean to a bloody pulp.

Yet there’s still a bit of that sarcasm and wit that Mark Pellegrino brings to the character that Jared Padalecki echoes in his own performance. It not only shows Padalecki’s strength as an actor but also illustrates why Lucifer Sam is entertaining, even when he’s terrifying.

2. Demon Dean

I could give you several reasons why Demon Dean is the best alternate version of Dean Winchester. I could dive into how important Dean’s time as a demon is to his relationship with Crowley, or discuss how the effects of Dean’s demonic actions are similar to his PTSD from being in Hell, or dissect Dean’s speech to Sam about how much he resents him.

But why would I write about any of that when watching Dean horribly sing karaoke best explains it all?

1. Soulless Sam

Soulless Sam is the best alternate version of Sam Winchester, and it remains one of the most inventive storylines Supernatural has ever done. Does every single moment during the Soulless Sam arc work? No, but the mystery surrounding what’s wrong with him and Dean and Castiel’s mission to bring him back to the person he truly is provided the first half of Supernatural’s first post-Kripke season with a creative jolt.

Plus, while Soulless Sam has a total lack of empathy for Dean and pretty much everyone else, he also delivers some of the most darkly funny moments ever on Supernatural, moments that ended up being comedy highlights from the show’s uneven sixth season.

Supernatural returns for Season 14 on Thursday, Oct. 11, at 8pm on The CW.

Chris King
Chris is a freelance writer with a passion for CW shows and a co-host of the podcast iZombie Radio. When he's not writing or podcasting, Chris spends his time eating spicy wings, cheering on the Philadelphia Phillies and Eagles, and re-watching the greatest film of all-time, 'Sing Street.'
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