Happy Birthday, Dean Winchester: Our Favorite Dean Episodes on ‘Supernatural’

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The CW

Contributors: Jules, Kenedi, Meredith, Brianna, Megan, Sarah W

Dean Winchester is a man with many sides to him. At various times, he’s a master monster hunter, huge nerd, loyal friend, sarcastic smart ass, and protective brother. Over the course of Supernatural‘s 327 episodes, we followed Dean as he grew from angry young man who lacked faith to a man who discovered the power of found family and embracing who you are. In honor of Dean’s 42nd birthday, we wanted to celebrate Dean by looking back on the series as a whole and choosing our favorite Dean episodes. While we can’t give the elder Winchester brother Rice Krispie treats in honor of the occasion, we wanted to celebrate the moments that shaped Dean, from the hilarious to the heartbreaking.

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“Dog Dean Afternoon”

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What do you do when the only witness to a murder is a dog? Well, if you are Dean Winchester, you perform a spell that gives you the ability to communicate with dogs to get the answers you need (where was this spell when Cas needed to interrogate the cat?). Sounds simple enough, right? What Dean learns is two things: he can communicate with all animals, and he can channel more dog-like behaviors than expected. We see him get in a yelling fight with a pigeon, bark at the mailman, play fetch, ride in the Impala with his head out the window, make whimper sounds, and more. You cannot help but laugh so hard you have tears in your eyes while watching this episode.

“Mint Condition”

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Even though Dean starts out wallowing and staying in his room eating pizza and watching movies at the start of the episode, we do get to see the nerdy side of the eldest Winchester make an appearance. It was nice to see Dean enjoy a case and behave in a childlike manner during this “monster of the week” episode. During “Mint Condition,” the brothers are on a case where action figures are coming to life and attacking people. They get to spend time in a comic book shop where Dean sees a life-size version of Hatchet Man from his favorite horror movie. We also get to see the Red Hood costume in the background, along with several other Easter eggs. Yes, his mood is due to avoidance of the recent events he has gone through with the archangel Michael (typical Dean behavior), but we will take happy Dean any way we can have it. Let’s face it, over the 15 seasons, there was not a vast amount of Dean being truly happy and enjoying himself.

“Last Holiday”

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We know that Dean’s childhood was not typical, to say the least. Hunting from when he was a child and killing for the first time at age 12, Dean missed out on so many milestones of being a kid. One of those was celebrating holidays like Christmas. We’ve seen him try to make Christmas nice for Sam before, but in “Last Holiday,” Dean finally gets to experience the holiday as a child would — with someone caring for him and making it perfect. His glee at seeing the bunker decorated, not to mention the look on his face when he is presented with the purple pajamas of his dreams, is a truly joyful Dean moment that is rare for the show. It’s all the more heartbreaking when Dean realizes that Mrs. Butters isn’t just a sweet old lady and is yet another person in his life with ulterior motives. But at least for a while, Dean got to have a normal childhood experience with true happiness.

“The Trap”

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Dean has had some incredible monologues on Supernatural, but his prayer to Castiel in Purgatory in “The Trap” is a standout. Dean so rarely investigates his own feelings, often pushing them down and covering them in sarcasm. But after he thinks he has lost Cas before getting the chance to say he was sorry, Dean breaks down and bares his soul in an uncharacteristically honest way. He talks about his anger, his deep sadness, and his confusion at why those emotions live inside him. For a moment, Dean isn’t the monster hunter out to kill God — he’s a scared man who is afraid that he made an irredeemable and irreparable mistake pushing away his best friend because of his inability to control his anger. It’s powerful to watch, and it marks a major milestone for Dean emotionally.


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One thing that can be said about Dean is that he is an obvious fanboy. Whether it’s obsessing over Western films or a horror movie icon, Dean’s geeky side definitely comes out over pop culture. When he and Sam get zapped into the TV in one of the most ambitious crossovers of all time, “Scoobynatural,” they realize that they are in none other than Scooby-Doo. This makes Dean very happy, and even more happy when they see the Scooby gang at a malt shop. He introduces himself while trying to play it cool, eating a huge sandwich that is way bigger than his mouth, then suggests they come along with them since they’re in the same business. One of the best parts of the episode has to be the race between Baby and the Mystery Machine, and, surprising Dean, the Mystery Machine won. Throughout the episode Dean wears a night gown that makes another appearance in “Last Holiday.” He shows his distaste for Fred and his affection for Daphne. At the end, Dean wears an ascot like the one Fred wears and we even get a “Scooby Dooby Doo!” It shows that even in the darkest of times in their lives, Dean still knows how to have fun and act like a kid.

“Who We Are”

Perhaps one of the most heartbreaking episodes for Dean is the season 12 episode “Who We Are.” As he, Sam, and Lady Bevell are trapped in the bunker with seemingly no way out, and losing air fast, Sam and Dean get their goodbyes ready after trying practically everything to get out. Dean comes up with the idea to finally use the grenade launcher, and in doing so, brings the bunker back up to how it originally was while injuring himself in the process. He and Sam get together the last remaining hunters they can find and make a plan to raid the British Men of Letters with Sam leading them. Dean stays behind to help a brainwashed Mary, going into her mind. Dean has to face all of his pent up anger towards Mary that he has had from when she made the deal with Azazel and ol’ Yellow Eyes came waltzing into Sammy’s room. Dean lets out everything in him, about what Mary did, what he and Sam went through, what John went through, all because of her. He hates her but he loves her at the same time. It’s a heartbreaking scene that shows the pain and burden that Dean has been carrying around with him for decades. It even saves both he and his mother as they and Sam are reunited once more.

“Yellow Fever”

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Poor Dean has a rough go of it in this episode when he gets infected with the very thing killing the victims they are investigating. This ghost sickness renders him terrified of literally everything. He refuses to rent a hotel room on the second story (it’s too high), sprints like a track runner when he sees a tiny, yappy Yorkshire terrier, and screams bloody murder when Sam opens a locker and a cat runs out. While it definitely becomes a serious issue toward the end of the episode, we can’t help but laugh along with Sam at Dean’s increasingly ridiculous fears. This was such a great episode where we got to see a different side (the terrified side) of Dean Winchester and we’re all the better for it!


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It’s no secret that throughout the seasons we’ve learned that Dean really is a nerd, and he loves anything and everything Wild West. During “Tombstone,” Team Free Will 2.0 catch a case in none other than Dodge City and Dean goes full nerd on the western themes. He books them into a themed hotel where he can’t stop talking about all the photos of famous Wild West cowboys on the walls including Wyatt Earp and Doc Holliday. Later we see him and Cas sporting boots and cowboy hats to the crime scene where we learn his love for old westerns means Cas was forced to watch Tombstone. Dean knew this was his one shot to revel in his love for the Wild West and we applaud him for going all out! Yeehaw!

“Bad Boys”

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Season 9 had a lot of action, with the mark of Cain and the civil war in Heaven. In “Bad Boys,” Dean and Sam travel to the boys’ home that Dean stayed at for two months when he was 16 to deal with a ghost. We love how Dean handled the case in this episode, mainly due to how he interacted with the child named Timmy. Dean protected Timmy from the bullies that were picking on him and made sure he knew that someone was on Timmy’s side. Sam may tease Dean about not being good with kids, but how Dean interacted with Timmy is sweet and proves that Dean is more than meets the eye.

“The End”

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This Dean-centric episode is one of his greatest. After Sam reveals his status as Lucifer’s vessel and Dean refuses to reunite, he is thrown into an alternate timeline where he never took his brother back. He runs into himself in the future, who tells him that Sam said yes. It’s heartbreaking to watch Dean see a hardened version of himself that doesn’t care about consequences, even if it costs someone their life. Our Dean’s shock at seeing what he’s done in this timeline is so painful to watch. Then there’s the future version of Dean. Future Dean was so desperate to fix things that he was willing to give himself up to Michael. The biggest heartbreak comes when Dean is face to face with Lucifer in Sam’s body. He can’t see his brother through the archangel in front of him and it always ends with Dean (and us) in tears. When he eventually returns to our time, it’s refreshing to see him reunite with Sam and realize that they’re stronger together.

“LARP and the Real Girl”

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This episode, while focusing heavily on Charlie, has some of our favorite Dean moments as well — it even takes place on his birthday! A lighthearted episode as compared to some of the series’ darkest moments, “LARP and the Real Girl” found Sam and Dean investigating mysterious deaths in Moondor, a LARPing community — which obviously requires them to join in (y’know, for undercover purposes). While on the case, Dean and Charlie reconnect and bond over LARPing; this episode is arguably when their iconic friendship begins (#besties). The audience gets to see Dean let loose in a way that he isn’t often granted the opportunity to, allowing his strategic prowess to blend with his inner geek in helping defend Moondor while also catching the baddie (hero gets the girl monster gets the gank, am I right?). Some of the most memorable Dean moments from this episode include Belladonna (if you know, you know), Dean strategizing with Charlie about where to move her troops, his iconic walk next to Charlie as the Queen’s handmaiden, clad in chainmail armor, and of course, who could forget Dean’s (stolen) speech as he charges into battle for Moondor after he and Sam choose to stay and LARP once the case is solved. Moments like these when you get to see Dean almost child-like with glee, unburdened by the weight that he had to take on so early in life, are scenes that we cling to dearly in our memories of the elder Winchester, as they only endeared us to him all the more.

“The One You’ve Been Waiting For”

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Dean Winchester is many things: a goof, a sweetheart, a man with an unnatural appetite. Despite all of these characteristics that show us the softer and more hidden side of Dean Winchester, one thing that you should never forget is that he’s a badass. Dean has racked up some pretty noteworthy kills over the years: Azazel, the Stynes, Ruby — the list could go on and on. However, one of Dean’s most badass moments to date would have to be killing Hitler. When the Thule try and revive the supreme Nazi fascist using one of his descendants, Sam and Dean burst on the scene to put an end to that … ASAP. While he doesn’t get to use the precious grenade launcher (though that does come later in the season in “Who We Are”), Dean effectively puts an end to the Thule’s plan by planting a bullet in one Adolf Hitler’s head, quipping “Heil this” in true Dean Winchester fashion before carrying out the deed. Such a monumental kill showcases Dean’s ability as a hunter — one of the best in the land. However, also in true Dean fashion, the elder Winchester did not let this feat go unnoticed, proudly bragging to anyone who would listen in the following episodes that he killed Hitler — as he should; it’s not everyday one kills one of the most hated men in history.

Honorable Mentions

The J Turn, “Baby”

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Hugging Miracle, “Carry On”

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He’s Batman, “Bad Day at Black Rock”

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Did we miss any of your favorite Dean episodes? Let us know in the comments!

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By Jules
I am a nurse and dedicated nerd from Boston, MA. When I'm not at work, I'm rewatching old favorites like Supernatural or discovering my new obsessions (too many to count!). When not fangirling, I can be found reading, writing, or listening to a true crime podcast. You can find me on Twitter @juleswritesblog for more nerdy nonsense.
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