These are the times Dean was the best “Supernatural” character. Our countdown includes mind over Michael, taste of fear, BFFs forever, and more!
For this list, we’ll be looking at some of Supernatural’s most memorable moments where Dean Winchester was our absolute favorite.
Which Dean moments stick out in your mind? Let us know in the comments below!.
#10: Mind Over Michael
After Lucifer takes Jack, Dean’s left with no other option than to finally accept being Michael’s vessel in season 13. Of course, despite the conditions the older Winchester tries to put in place, the alternate version of the archangel reneges on the deal, forcing Dean to imprison Michael in his brain. While at a diner in Season 14, Castiel notices the toll this Michael problem has taken on his friend. Dean doesn’t only admit that he doesn’t know if he’s fine, but he also describes the sheer will power it takes to keep Michael at bay. Though Cass reminds Dean he isn’t alone, Dean responds with three little words that demonstrate the depth of his selflessness and his willingness for self-sacrifice to prevent Michael from getting loose.
Demon Dean was a treat for fans because we got to see Dean be a total dick. After dying with the Mark of Cain, Dean comes back to life as a demon at the end of Season 9. This new version of Dean is selfish and all ego, a creature of pure impulse and satisfaction. A way more violent character, Demon Demon seemed to enjoy the ruthlessness that came out when he didn’t get his way. While our time with Deanmon was brief, it was fun to see Jensen Ackles play almost the opposite of the character we’ve come to associate with him. This Dean even went as far as to claim he didn’t care about the life of his brother Sam and to refer to the Impala – his “Baby” – as “just a car.”
#8: Taste of Fear
Despite being a CW show, Supernatural has some pretty spooky moments. Dean is often portrayed as this macho, alpha male type character who tends to rarely be phased by anything. One of the best moments of the whole series is in Season 4. In “Yellow Fever,” the brothers are investigating the deaths of a few townspeople and Dean gets affected by a sickness that makes him fearful of everything. It starts out with anxiety, but progresses to full blown panic and then eventual death. This episode thus totally flips Dean’s characterization and leads to some hilarious moments along with the aforementioned spooky ones.
#7: Deep Death Pizza
“Two Minutes to Midnight”
There have been some monumental moments in Supernatural, but very few come close to Dean and Death’s first meeting. Not only was the introduction of this Horseman of the Apocalypse one of the most unforgettably intimidating moments of the series, but the subsequent conversation between Death and Dean also shows the former’s superiority over the latter. The ancient primordial entity treats Dean like nothing more than a blip in time and has little time for his questions. While Death is likely deserving of his own Top 10 list, what makes this scene ultimately work is Dean’s ability to keep his cool in the face of literal Death.
#6: Everyone’s Time Traveling Dream
“The One You’ve Been Waiting For”
Pretty much everyone has wished to do this, and as it turns out, Dean is the one who gets to live out everyone’s fantasy of killing Hitler in this season 12 episode. After Hitler’s soul is put back into a physical body, Dean has the enormous pleasure of sending one of history’s worst to hell. Sending off the resurrected Führer with a bullet and an appropriate one-liner, Dean becomes instantly elated with his actions, and relishes the fact that he gets to say that he killed Hitler. Dean tells Sam that he isn’t planning on letting this go, and makes sure to bring it up whenever possible in subsequent episodes. Like, seriously: he won’t shut up about it; but, in all honesty, can we blame him?
#5: A Soul for a Brother’s Life
“All Hell Breaks Loose (Part 2)”
Dean has always been about protecting his little brother, and when he fails to do so he’s left wondering what else he is supposed to do. In the Season 2 finale, Dean summons a demon to make the ultimate deal following a fit of pure rage and emotion. Dean is so desperate that he’s willing to sell his soul to the very creature he’s sworn to eliminate — all for the chance to save his Sammy. While the usual deal is 10 years of life, this demon isn’t so generous and forces Dean down to just one year to live in exchange for Sam’s life. Despite the lousy terms, Dean makes the deal, and shows us the extent of his brotherly love.
#4: Ruh-Roh Dean
Mystery Inc. has had a lot of weird crossovers, and one of the best on that list is with Supernatural. On top of “Scoobynatural” just being a really great episode, no one is more excited for this this cartoon melding of worlds than than Dean. After getting transported to an episode of Scooby-Doo, Dean couldn’t be more ecstatic to meet Scooby-Doo and the rest of the gang. This Supernatural episode is filled with laughs due to both shows having to adapt to the other, and it leads to some truly great scenes. Dean fully embraces the tropes of the animated TV series, even trying to flirt with Daphne a couple times. The cherry on top is when Dean attempts to end the episode just like Scooby normally does after they solve a case.
#3: BFFs Forever
Cass has been training in heaven to enact the angels’ plans, and one of the things that he needs to learn to do is defeat Dean. He and Dean have an incredible bond, almost as strong as Sam and Dean’s, which makes it hard for Cass to sever. When the moment finally comes, Cass can’t do it, which means that Naomi takes control of him – and she doesn’t hold back. In a plea to get him to snap out of it, Dean tells Cass exactly how much the angel means to him. The moment is especially noteworthy because it reaffirms to both the characters and the audience that, even after all they’ve been through, Dean still cares this much about him.
#2: ‘Tis Better to Have Loved and Lost…
“Let It Bleed”
After Sam’s sacrifice at the end of Season 5, Dean promised him that he wouldn’t try to bring him back, and that he’d settle down and be normal. Dean keeps his promise and meets Lisa and Ben. They end up together and for a while it seems like Dean will have a calm life. Of course, this is Supernatural and that’s never the case, as Sam comes back and the boys head out again on the hunt. After Lisa and Ben are almost killed, Dean decides to make them forget who he is. He asks Castiel to erase their memories in the hopes that this’ll keep them safe. Dean almost had the perfect life, but once again makes a tough choice for the greater good.
Before we unveil our top pick, here are a few honorable mentions.
“Dodge, Duck, Dip, Dive and Dodge”, “After School Special”
Dean Would Make One Hell of a Gym Teacher
Master of Disguise, “Sam, Interrupted”
Dean Does His Best to Blend in at the Psychiatric Hospital
“I’m Batman,” “Bad Day at Black Rock”
Not Sure About Batman, But Dean Would Definitely Make for a Great Robin
Dean’s Love for Pie, Various
A Red-Blooded American
“Wanted Dead or Alive,” “No Rest for the Wicked”
It’s Never a Bad Time for Some Bon Jovi
#1: Sam Over Everything
For most of the story, Dean’s been the most consistently committed to the mission, as it’s all he’s known. In Season 9, it’s revealed he took a step away from the Family Business when he was sent to a boys’ home after some bad behavior. Even more surprising is that he seemingly thrived there. Things obviously didn’t stay that way forever, as John and Sam eventually came to get him – though Sam thought Dean had been on a hunt. Despite Dean’s success, he chooses to leave the home and it’s implied he made the decision to keep an eye on his little bro. Dean could’ve had a whole different life, but even at 16, he knew Sam was the most important thing to him above everything else.