What are the best Dean Winchester moments on Supernatural?
In the early noughties, a weekly show about demon-hunting brothers may have seemed like a bad joke, but Supernatural turned fans around swiftly with the unforgettable dynamic between its protagonists.
Dean Winchester (Jensen Ackles) and his younger brother Sam (Jared Padalecki) couldn’t be more unlike each other. Dean is brash, often uncouth, and loves hunting. Sam, on the other hand, is cerebral and has always dreamed of having a normal life.
Forget demons, ghosts, and ghouls, viewers were immediately sold on this unlikely pair and their road trip to save the world.
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Much of the show’s appeal lies with Dean—humorous and sometimes goofy, Dean is the definition of the hero with a heart of gold.
Dean has never shied away from making the tough decisions even if it mars his soul—as long as he can save the people he loves and the world, he’s ready to risk it all.
But it is Dean’s unwavering loyalty and love for his brother that has kept fans engaged for 15 seasons. There is nothing in the world that Dean Winchester wouldn’t do for his little brother and that elevates him above the stereotypes that could have shackled him.
Now that the show is ending after a 15-year long run, we look back at Dean Winchester’s greatest moments. This was a hard one for us, because not only is Dean a layered character, but he is played with effortless passion by Jensen Ackles.
Ackles has the ability to infuse Dean with great humor and immense pathos. He is talented enough to have viewers guffawing in one scene and turning into blubbering crybabies the next. So, which Supernatural favorites made it into our top 15?
15. LARP-ing Dean Winchester
Dean Winchester doesn’t often get the chance to let his hair down, but when he does, he takes that opportunity with both hands.
In ‘LARP and the Real Girl’, Sam and Dean meet up with fan-favorite supporting character Charlie (Felicia Day), one of the rare queer characters represented on the show. Charlie is a geek through and through and takes to LARPing (live-action role-playing) in this Season 8 episode, to escape the hunting life.
When LARPers end up dead, Sam and Dean are at hand to investigate. After discovering a magical world, complete with a damsel in distress who is saved by Charlie, the brothers make good on their promise to Charlie—to join her army and help her win the game.
Dean, in full Braveheart regalia, complete with war paint and lustrous wig, delivers William Wallace’s battle cry from the film with aplomb. One can tell that Dean takes every fight seriously, including fictitious ones. This fight is no different.
What sells the scene is Ackles’ dedication to reproducing the speech with the same passion and charging into battle as though he’s been transported to the 13th century. What could have been a forgettable episode is made indelible by the showrunners embracing the sillier side of Dean?
14. Dean Winchester Befriends Benny the Vampire
If there’s one thing we know about the Winchester brothers, it’s that they hate the monsters they hunt. Vampires, werewolves, and demons have no redeeming qualities in the Winchesters’ eyes. While the brothers’ outlook has mellowed over the years, back in Supernatural Season 8, there was no love lost between Dean and the monsters.
All that changed when Dean was trapped in Purgatory. Fighting to survive on his own, Dean got a helping hand from Benny the Vampire (Ty Olsson). Benny and Dean’s friendship, though short-lived, proved how much Dean had grown from his single-minded mission as a hunter.
The two became blood brothers and Dean took several chances to bring Benny back to the real world. Dean later fought tooth and nail to clear Benny’s name, even going as far as to clash with Sam about Benny’s innocence.
In the end, Benny was unable to fit into the real world and Dean had to make the ultimate sacrifice play, kill Benny and send him back to Purgatory. At least Dean allowed Benny to go out on his own terms.
Dean’s closeness to Benny has come up several times over the course of the past few Supernatural seasons, and it’s evident that Dean still struggles with this immense loss.
13. Dean Winchester Turns Down Michael
In Season 5 of Supernatural, Lucifer’s rise could be stopped by only one person, the archangel Michael. While Lucifer’s true vessel was Sam, Michael’s was Dean.
When his brother Sam and half-brother Adam (Jake Abel) is captured by the evil the Angel Zachariah (Kurt Fuller), Dean must decide—agree to become Michael’s vessel or watch his brothers die. With no other option, Dean accepts Zachariah’s offer.
Now, the problem with becoming a divine vessel is that the human is pretty much toast when the being leaves the host body. The rules have been bent a little over the course of the show, but at the time, Dean was sentencing himself to death.
But he’s smarter than he looks. With a sneaky little wink to Sam, Dean gets Zachariah close enough to stab him with the Angel blade. As Michael descends to Earth, Dean grabs injured Sam and they rush out of Zachariah’s hideout.
Unfortunately—and this is the reason the moment is so low on our list—Dean fails to grab hold of Adam on his way out. Instead, Adam is trapped in the room and forced to take Dean’s place as Michael’s host.
But you can tell Dean is despondent by what’s happened. The look of horror and loss is another example of Ackles’ superb acting abilities.
12. Dean Winchester Refuses to Give Up on Castiel
Dean and Castiel (Misha Collins) have a long-standing friendship beloved by fans. They haven’t always seen eye to eye, but Cas is family for the brothers.
When, in Supernatural Season 8, Cas was led down a dark path by a fellow Angel, he turned against the Winchesters. In ‘Goodbye Stranger’, Cas rehearsed killing Dean in simulations over and over to grab the demon tablet from him.
Once the chance to kill Dean presents itself, Cas seems close to succeeding. But Dean’s plaintive pleas save his life. During the 15 seasons of the show, we’ve seen that Dean Winchester is willing to take quite a beating from the people he loves because, in the end, he’s always able to snap them out of whatever’s making them hurt him.
With Cas looming over him with a fist and the angel blade, Dean reminds him that ‘this isn’t you’ and that the Winchester brothers need him; Cas is their family.
Cas finally relents, healing Dean and even apologizing for hurting him. The show’s writers never shy away from how much faith Dean has in the people closest to him. It’s no wonder ‘Destiel’ is such a huge favorite among fans. They’ve gone through hell—or rather purgatory—and back and they remain friends and brothers to this day.
11. Young Dean Winchester Goes Back to Hunting for Sam
The key to the success of Supernatural is Sam and Dean’s relationship. Despite being set in a fantastical world, the bond between the two brothers grounds the show emotionally.
While we see plenty of these instances between adult Sam and Dean, one of the most heartbreaking moments is from a flashback. Young Dean always grated against the hunting life that his father John Winchester (Jeffrey Dean Morgan) dragged the boys into.
In ‘Bad Boys’, we learn that young Dean once had to steal food to feed his brother and ended up being sent to a boys’ home. The owner gives Dean a permanent spot for him to stay and this proves to be a more stable environment for the young boy. Dean surprisingly excels at school, makes friends, and plans on a future that doesn’t involve hunting.
When he falls for a girl his age, Dean makes the decision to remain in the small town. But the moment John returns, with little Sammy waiting eagerly for his brother, Dean turns away from the life he so desperately wants and leaves in the Impala.
As if young Dean’s decision isn’t heart-wrenching enough, older Dean lies to Sam about why he left. Not wanting Sam to feel guilty for ruining Dean’s chance at living a normal life, Dean jokes that he couldn’t wait to get out of this place.
10. Dean Winchester Gives up Lisa and Ben
The sixth season of Supernatural was a tough one. Creator Eric Kripke had a five-year plan, but the show was greenlit for a new season, which eventually gave the Winchesters another decade of life.
While the season fumbled along, one constant was Dean hanging onto the domestic happiness he’d found with Lisa Braedon (Cindy Sampson) and her son Ben (Nicholas Elia). Lisa and Dean’s relationship had been set up way back in the third season, and when Dean followed through on his promise to give up hunting if he lost Sam, the person he turned to was Lisa.
Ben loved Dean like a father and Lisa was willing to put up with his comings and goings. Throughout the season, Lisa remained a pillar of support for Dean.
Unfortunately, you can leave the hunting life, but it doesn’t leave you. Dean tries his best to protect Lisa and Ben, eventually breaking off his relationship with them. Despite this, Lisa and Ben are almost killed, leaving Dean with no choice. In ‘Let It Bleed’, he asks Castiel to erase their memories of him to protect them from his day job.
His last interaction with them sees him apologizing for ‘crashing his car’ into them. And with that, Dean bravely closes the door on his longest-lasting relationship.
9. Dean Winchester and Death Share a Pizza
Only on Supernatural would a character enter a diner and meet the living personification of death, and no one would bat an eyelid at this occurrence.
While the exchange between Dean and Julian Richings’ Death isn’t a match for The Seventh Seal, it’s Dean’s ability to have a conversation at all that’s impressive. Ackles plays Dean as understandably terrified but also opportunistic.
It’s hilarious that we can see Dean chomping on pizza during the discussion. Death is calm and nonchalant, only losing his temper when Dean’s inflated sense of self gets annoying. In Dean’s defense, the world rests on his and Sam’s shoulders, so he’s allowed to believe he’s important.
Dean is lucky to be alive because Death needs his help to end Lucifer’s control over him. Dean plays his cards right—he’s eager to save the world, yet he’s curious about the being in front of him as well.
Dean walks away with what he needs, but with the promise that he won’t stop Sam from becoming Lucifer. As we all know, Dean tries his best to do exactly that, but fails.
Death’s warning that Dean ‘can’t cheat death’ has become an unspoken joke on the show. The boys have died innumerable times and Dean, in fact, goes on to kill Death when he tries to make the brothers murder each other.
8. Dean Winchester’s Memorable Entrance
As introductions go, Dean Winchester has one of the more unexpected ones we’ve seen on television. The heroics in Dean’s future are but a distant dream in the pilot episode of Supernatural.
Dean is introduced to audiences by breaking into his brother’s apartment, getting into a fight with Sam, and only revealing himself when he gets the upper hand over Sam. His first spoken dialogue on the show? “Whoa! Easy Tiger.” Accompanied by a cheeky and infectious smile that continues to melt hearts. If that isn’t Dean, then what is?
This moment leads us to one of the most memorable sequences from the show. Dean mentions their dad has gone on a hunting trip and hasn’t returned. This cryptic piece of dialogue—that makes so much sense to the brothers but not yet to the audience—is the launchpad for the rest of the show, and fans are sucked into the lives of the Winchester family for 15 more years.
From the get-go, it seemed like Ackles had a complete understanding of the character—nothing Dean does in that first episode can be refuted by fans who’ve been with the show ever since. The ability to be so true to a character that was essentially cemented in his opening scene is astounding, and Ackles has done the role proud.
7. Dean Winchester Needs Sam to ‘Fight those Fairies’
In Season 6’s ‘Clap Your Hands if You Believe’, Dean and Sam find themselves investigating alien abductions—but this being Supernatural, the culprits are exposed as being more down to Earth, albeit magical.
Having been ‘abducted’ by the aliens, Dean continues to look for answers but finds himself being followed by a suspicious character. He turns through alleyways and gets a jump on the guy, only for it to turn out to be someone completely innocent. Oops.
Of course, this leads to Dean being arrested. It’s nothing he hasn’t handled before, but there’s a case to be solved so he shouts some final instructions to Sam before being taken away. “You fight those fairies, Sam!” Cue a commercial break because every viewers’ laughter will drown out the next scene.
Ackles’ moments of humor on the show are so well-timed and enunciated that one can forget that Supernatural was meant to be a horror story. And what makes this scene even funnier is that Dean is completely serious in his request since he’s made a breakthrough in the case and he needs Sam to do the work while he’s incarcerated.
But for everyone watching—including the arresting officer—seeing a man randomly scream about fighting fairies is confusing and hilarious.
Considering that this episode takes place during a terrible time in the Winchesters’ lives—Sam is soulless, and completely lacking in empathy, which puts Dean in a terrible position—these bright sparks of humor from Dean are a much-needed balm both for him and the viewers.
6. Dean Winchester Protects Sam from Scared Townspeople
The first few seasons of Supernatural had scarier episodes than its successors. One of the eerie ones was ‘Croatoan’. When a demon virus infects an entire town, Sam and Dean must try to save the survivors and themselves.
Unfortunately, one of the infected bleeds on Sam, leading the medical staff to believe Sam is infected. Everyone’s immediate reaction is to kill Sam and stop the spread, but once again Dean jumps in to protect his brother.
Even Sam is terrified of turning into a demon-zombie, but Dean remains adamant that Sam will be fine. Admittedly, Dean is in the denial stage of the situation, but it doesn’t stop him from hoping for the best.
Dean goes as far as to remain with Sam while the rest of the townspeople escape in his beloved Impala, Baby. At this time, Dean is also carrying the weight of his father’s final diktat—to kill Sam if he can’t save him.
When Sam insists on ending his own life, Dean suggests he might go down with Sam. He’s tired of living a life where he is scared for his brother’s safety all the time.
In the end, Sam turns out to be immune to the virus due to the Yellow-Eyed Demon, but Dean’s heroics cement his place as one of the best TV brothers.
5. Dean Winchester Keeps Michael Locked In
Season 14 was a topsy-turvy time for the Winchester brothers. Every win came with a loss, none more so than the good guys defeating Earth-2 Archangel Michael, only for him to possess (and re-possess) Dean’s body.
As we learned in earlier seasons, Dean was Michael’s true vessel. This may have made Dean a comfortable meatsuit for Michael, but it also made him impossible to eject without killing Dean.
Michael proves to be a destructive force irrespective of which Earth he is on, which means Sam, Dean, and Castiel must contain him somehow. When every option fails, it’s up to Dean to make the tough decisions.
Dean’s heroic moments in this season are two-fold – his willingness to spend eternity trapped in a coffin at the bottom of the ocean, with Michael in his head; and his valiant fight to keep Michael trapped in his head above ground after Sam pleads with him to stay.
Ackles’ ability to portray real emotions in a supernatural show comes to the fore every time we see snippets of Michael hammering his way out of Dean’s head. Dean’s strength to not only keep the beast at bay but to hide his pain from his loved ones is what makes us love this character even more.
4. Dean Winchester Makes a Deal for Sam’s Life
Sam and Dean’s often tumultuous, but realistic, brotherly bond has been the key reason fans continue to tune in to the show. One of the earliest moments that demonstrates Dean’s unwavering love for his little brother comes in the finale of the second season of Supernatural.
In “All Hell Breaks Loose – Part 2”, Sam is felled during a Battle Royale set up by the Yellow-Eyed Demon. The creature, that cursed Sam when he was an infant, leaves Sam to die in Dean’s arms.
The scene puts Dean and the fans through the emotional wringer. How could this happen to the main character? How can Dean cope with the death of his ‘Sammy’?
Unable to accept the loss of his brother, Dean makes a deal with a crossroads demon. For the cost of his soul, the demon resurrects Sam. Dean is given a year to live before he will spend eternity in Hell. Dean doesn’t hesitate to take the offer.
The sacrifice sets up the third season’s central emotional conflict, but more than that drives home the extent to which the brothers will fight and sacrifice to keep each other safe. In the case of Dean, his protective nature as the older brother comes to the fore. He practically raised Sam and he refuses to give him up without a fight.
3. Dean Winchester Gets Yellow Fever
Supernatural is an entertaining show, but while it rides high on the emotions of its characters, some of its best moments—and episodes—are the comedic ones. High on the list of comic episodes is ‘Yellow Fever’, a highlight reel of Jensen Ackles’ superlative comedic talents.
While investigating a ‘ghost sickness’ overcoming the people in a small town, Dean is infected as well. The sickness leads him to fear everything. From crossing the street because he doesn’t like the look of some kids to screaming at the top of his lungs at the sight of a hidden cat, Dean is left quaking in his boots.
Since the sickness affects people who are jerks, the entire episode is a masterclass in subverting the trope of macho male leads. It’s a laugh riot because viewers never know when Dean’s dialogue is going to have us in splits. One of the best moments in the episode is when Dean high tails it out of ground zero as soon as a ghost appears. The way the scene is shot is perfection.
Bottle episodes like this one also give characters a moment to reflect on their crazy lives. Dean’s hilarious but poignant appraisal of the brothers’ hunting lives is funny because it’s true. Who actively looks for a monster to kill them? You should run!
To top it all, ‘Yellow Fever’ ends with Ackles lip-syncing “Eye of the Tiger,” a fun little behind-the-scenes moment for fans to enjoy after being on high alert for 40 plus minutes.
2. Dean Winchester’s Passionate Speech
In Season 8, Sam and Dean stumble upon a possible way to seal the gates between Hell and Earth and end the barrage of monster attacks. As Sam undergoes the three Trials, Dean discovers that the final trial will lead to Sam’s death.
Yet when Dean reveals this information to Sam, he shrugs it off with “So?” Sam is too disillusioned by how much he’s failed Dean to care about living any more. According to Sam, Dean is better off without him, and he’ll have other more powerful people to lean on. But Dean refuses to let his little brother go, even if it’s for a greater good.
Dean’s impassioned plea to Sam is some of the most emotional minutes you’ll see on any show. Ackles delivers each line with heated perfection, especially this one:
“Don’t you dare think that there is anything, past or present, that I would put in front of you!”
The entire exchange between the two brothers is extremely impactful. What sells it is how much Dean is willing to forget and forgive to save Sam. Sam hasn’t always been the best brother, which is what makes him like most other siblings in real life. Dean believing in Sam irrespective of his flaws is as realistic as this show gets.
1. Dean Winchester Sings “Dead or Alive”
Dean’s journey to Hell is paved with the brothers’ desperate hunt for a way to break the crossroads deal. Once Sam learns of Dean’s deal, he is certain they can find a way to save Dean.
As the third season comes to a close, it becomes evident that perhaps the Winchesters’ luck might have run out. With Hell’s doors waiting, in the Season 3 finale “No Rest for the Wicked”, Dean pleads with Sam to make peace with the deal.
Ever the older brother, instead of ignoring Sam’s fear, Dean starts up a loud rendition of Bon Jovi’s “Dead or Alive.” He sings to distract Sam, before Sam joins the sing-along, allowing him to channel his emotions into the song.
But, while Sam sings, Dean’s face falls and fear engulfs him. He won’t let Sam see how afraid he is, but Dean allows himself this brief moment to confront how he really feels about what lays ahead.
The scene is one of the earlier testaments to Ackles’ outstanding acting abilities. His look of horror could have been comical, but Ackles perfectly captures the sense of doom Dean is feeling.
The entire segment is an emotional rollercoaster as we, the audience, are placed in the shoes of two loving brothers accepting the fate of one.
There you have it, folks—Dean Winchester’s best moments on Supernatural. Which moment is your favorite? Tell us in the comments below.
Supernatural Season 15 will air on The CW from October 8.