10 Best Dean Winchester Episodes of Supernatural

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With hundreds of episodes to choose from, narrowing down Dean’s best stories isn’t easy. But we feel that the following ten episodes highlight his humor, heartbreak, and heroism better than any others.

10) “Dog Dean Afternoon” — Season 9, Episode 5

Let’s start with some lightheartedness. Supernatural fans love when the show is able to find the funny amongst the serious and lean into its quirky humor, and “Dog Dean Afternoon” is one of the best. Dean tends to be the more brooding of the two (unless there’s a hot-looking distraction around), and so when his steely demeanor — or DEANmenor disappears, it’s always a nice break.

When the Winchesters create a spell for Dean to be able to communicate with dogs, viewers get to watch Ackles fully commit to canine characterization. Playing fetch, barking at the mail man, even checking out a poodle at one point. The episode balances its humor and standard show horror well, and Ackles manages to make an absurd situation feel like a milk run.

9) “Lazarus Rising” — Season 4, Episode 1

“Lazarus Rising” marked one of the most iconic moments in Supernatural history when season four opened with Dean’s resurrection from Hell. This also served as the series debut for Castiel (played by Misha Collins) and sets up the angel mythology that would shape the rest of the show. Many see it as one of the best cold opens in television, and it’s easy to see why. Dean’s return —digging his way out of his own grave like Beatrix Kiddo in Kill Bill — remains one of the show’s most unforgettable images. The stunt itself was no mean feat either.

Ackles has discussed the scene whereby they dug a hole 5-foot by 4-foot, and covered the top with neoprene and a boat load of dirt. He had to crouch, waiting until they called action. Not fun at all. But it’s not just the grave scene that makes this episode list-worthy. The story’s narrative overall is also well created, keeping the audience just as in-the-dark as Dean. We follow him as he tries to understand what happened, how it happened and why the time passed on Earth is literally only a few months compared to his 40 years in Hell.

8) “LARP and the Real Girl” — Season 8, Episode 11

This list isn’t just for the episodes where we laugh at Dean’s expense or acknowledge his stern, serious moments. Dean may be a gruff hunter, but “LARP and the Real Girl” proves he’s also a total nerd at heart. Let’s be honest, he never had the chance to be a kid, and every season has given us glimpses of his inner child (the rainbow slinky, anyone?), but in this episode, he’s really not great at hiding his boyish excitement.

The episode reunites the brothers with fan-favorite Charlie Bradbury played by the magnificent Felicia Day, who introduces them to the world of live-action role-playing. Dean — ever determined to keep his “cool guy” persona — cracks pretty quick and soon indulges in floon (meaning he’s super excited to be involved, for you non-LARPers out there). It’s definitely one of the most entertaining episodes of Season 8, and for good reason.

Watching Dean embrace medieval cosplay — complete with a fake sword — and leading the charge with an epic battlefield speech at the end of the episode, is pure joy. Dean not only gets to cut loose, but we also see him bond with Charlie like she’s his long-lost sister. This episode sets up one of the most genuine and enduring friendships of the entire series.

7) “Mint Condition” — Season 14, Episode 4

And we get to Dean’s geeky side again in “Mint Condition”. This episode serves not only as a love letter to horror, comics, and geek culture, but it’s the perfect setting for a Dean Winchester episode. Set on Halloween (Sam’s least favorite holiday, besides Christmas), the episode follows Dean and Sam as they investigate paranormal activities surrounding haunted objects that kill the staff of a comic book store. When the brothers turn up, Dean is immediately in his element as he fawns over a 7-foot-tall horror movie action figure from his favorite franchise. Unfortunately (or fortunately, for Dean’s fanboy mindset), the figure comes to life, and he has to try and fight it off.

6) “The End” — Season 5, Episode 4

But it’s not all fun and games. In “The End”, Dean is transported to a post-apocalyptic future where Sam has become Lucifer’s vessel, Castiel is some disillusioned love guru, and “Future Dean” has hardened into a ruthless leader, estranged from his younger brother. The episode allows Ackles to play out the duality of a present-day Dean and his colder, future counterpart.

It is one of the best explorations of Dean’s character, showing what might happen if he abandoned his compassion, and doubled down on his stubborn need to always be right. It’s a powerful contrast that proves Dean’s humanity is fragile, and heavily reliant on those he loves keeping him grounded. It also serves as an opportunity for Dean to confront his own internal fears, externally. His arguments and attempted reasoning with the (even more) self-destructive version of himself from 2014 gives him a perspective that helps him learn more about his own psyche.

5) “Faith” — Season 1, Episode 12

“Faith” is a very early example of Dean’s emotional growth. Long before angels and apocalypses, this episode established that Dean Winchester was indeed capable of emotional depth. After getting electrocuted Dean permanently damages his heart. With one month to live and no apparent fix, Sam finds a way to save his brother. He takes Dean to a preacher who is touted as a true faith healer, and performs healing miracles on all who come forward.

As luck would have it, Dean is miraculously healed. Afterwards, he begins to notice that things aren’t quite right — completely healthy people are dropping dead. It’s then he learns that the healer’s wife is secretly using black magic to control a Reaper. But where there’s death, there must always be death. “Faith” helped shape Dean into more than just a tough hunter, it showed his fear of being vulnerable and his lifelong struggle with self-worth. It just shows that Kripke was playing the long game in revealing his complex character.

4) “In My Time of Dying” — Season 2, Episode 1

Another earlier example of Dean learning some compassion comes in “In My Time of Dying”. Few episodes capture the emotional stakes of Supernatural like it. After being critically injured in a demon-caused car wreck, Dean finds himself in a spirit form, patrolling the hospital as his body is caught between life and death. The episode also tackles his and Sam’s relationship with their father John Winchester (played Jeffrey Dean Morgan) to the forefront, culminating in John’s ultimate sacrifice, and setting the trend for the Winchester family to keep making dodgy deals with demons, and upsetting Death in the process.

It’s another memorable season opening episode with its emotional resonance. It highlights Dean’s struggle with mortality, and his constant terror that he’s failing his brother — the one thing his father always told him never to do. Not only that, but it becomes a teachable moment for Dean where he finally begins to see supernatural and paranormal entities such as ghosts as more than just monsters.

3) “Frontierland” — Season 6, Episode 18

Back to the more wholesome elements of the elder Winchester. Dean’s childhood love of Westerns finally pays off in “Frontierland,” which sees the brothers sent back in time to find Samuel Colt’s Demon killing gun in the Old West. Dean, naturally, is in his element geeking out over (wildly inaccurate and overly clean) cowboy gear, quoting various Western-themed pop culture references, and living his gunslinger fantasy.

The episode is a welcome slice of fun in an otherwise heavy season. And anyone who’s a fan of the Western genre in any form can have some real fun with the Easter egg quotes. From him calling himself Eastwood, in both a nod to the actor, and a reference to Back To The Future III, John Wayne’s “Howdy Pilgrim” as well as the easy to miss “Candygram for Mongo” line straight out of Blazing Saddles. Dean’s sheer enthusiasm for being in a Western setting makes “Frontierland” one of his most charming and entertaining adventures.

2) “Yellow Fever” — Season 4, Episode 6

Now, we did say this list wasn’t just a chance to laugh at Dean’s expense, but we’ve got to make an exception for “Yellow Fever.” Dean contracts a ghost sickness that heightens his fear until it it will give him a heart attack and kill him. The result is an hour of comedy gold, with Dean running from Yorkshire Terriers, screaming at cats, panicking over a group of teenagers chatting, and driving Sam absolutely insane.

The episode is remembered for Ackles’ over-the-top performance, especially the now-legendary scream when a tiny kitten jumps out of a locker. Many fans and critics rank it among the funniest Supernatural episodes ever, and put Jensen Ackles in the lip sync hall of fame for his iconic Eye Of The Tiger outtake.

1) “Regarding Dean” — Season 12, Episode 11

But, we get serious for the top spot. “Regarding Dean” is one of the most heartbreaking Dean-centric episodes of the entire show. After Dean gets hexed during a run in with a witch, he starts to lose his memories. It starts as a humorous episode with Dean becoming lighter, even childlike in nature when he starts to rediscover everything for the first time again, even being endearing to Rowena. But the entertainment quickly turns dark as Dean’s loss of memory gets very real, with the threat of him eventually forgetting how to breathe.

It is an emotional home run, and Ackles’ acting chops are on full display in this episode. The scene where Dean repeats a short list of facts in the bathroom mirror, then the look of genuine terror and confusion on his face as he can’t even do that, is hauntingly real. The performance is honest, emotional and incredibly respectful of those who have experienced it in their loved ones. It’s a real testament to the actors and creators that they can produce such heartfelt moments.

What are your favorite Dean-centric episodes? Let us know in the comments!