Our Favorite Moments From ‘Supernatural’ Season 14: Dean Winchester

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Image courtesy of 'Supernatural'

Here we are, the final entry in our “Favorite Moments from Supernatural Season 14″ series, which can only mean one thing — welcome to the end. Our final spotlight is the one and only Dean Winchester, with his love for pie and his noodle socks and classic rock cassettes. Go kick it in the ass, Dean, there’ll be peace when you are done. Us on the other hand … I don’t think peace is the word. So without further ado, our staff’s favorite Dean Winchester moments.

Image courtesy of ‘Supernatural’


We have seen many sides of Dean over the past 14 seasons. We have seen him be tough, be the martyr, be the flirt, be the sarcastic one, and have even seen him geek out. But with Jack introduced, we have see a new side of Sam, Dean, and Castiel: the father side. Each of them has taken on a parental role taking care of Jack and teaching him things. Which leads to my favorite scene in “Unhuman Nature.” With Jack dying, he wants to experience life to its fullest, and who better to teach him than Dean! As protective as Dean is of Baby (he barely even lets Sam drive!), he teaches Jack to drive on a long stretch of road. There are smiles, jokes, and laughs! It is maybe the sweetest scenes in all of the series. And the heartwarming moments do not end there. Dean takes Jack fishing, and they have a heart-to-heart. But there is that underlying feeling that it is something Dean used to do with John, and now he is doing it with Jack. I loved watching this domestic side of Dean, and him showing how he truly will do anything for his family!

Image courtesy of ‘Supernatural’

Michelle C. 

There was so much to love about Dean and Jensen Ackles’ portrayal of him this season. Melanie mentioned his tender parental side with Jack, so I’ll go in the opposite direction and talk about Dean and his father. The 300th episode of the show titled “Lebanon” brought back Jeffrey Dean Morgan as John and the moment he showed up on the screen, I knew I was going to be a bawling pile of goo by the end. And I was. While it wasn’t shocking to us super fans, getting his father back was definitely a jolt to Dean. I mean, he was using a wish-granting pearl to help him get what he wanted the most — to get rid of Michael — and what he got was his father in the flesh. Every scene with Dean and his Dad was dripping with emotions and what-ifs. Got me right in the feels. And when Dean realized he had to say goodbye to his father again for the greater good, it was more than my poor heart (and Dean’s) was ready to take. I love that he finally got a sense of closure with John after all these years of following in his footsteps. It felt right and it felt like Dean found a way to bury a few demons of the figurative kind in that moment.

Another amazing Dean moment came in the finale. I can’t stress how much I loved that entire episode, but Dean smashing Chuck’s guitar? Priceless! Fed up Dean is a Dean I can always support. I swear, if I’m ever lucky enough to make it to a con and get a photo op, I’m bringing a thrift shop guitar and having them recreate that moment!

Image courtesy of ‘Supernatural’


We have not seen a carefree Dean Winchester in a long time. So, to see him geeking out in “Mint Condition” was a treat. You are considering up to this point Michael possessed him and even began the episode closed off in his room because he did not feel at home. To see Dean, get excited about the case was seeing a glimpse of the Dean not buried under all the weight he carries on his shoulders. When they arrive at the comic store and Dean sees the life-size Hatchet Man that speaks when you press a button, he turns childlike geeking out with the shop owner. Obviously after going through 14 seasons worth of monsters, death, apocalypses, hell, and more you would harden and be more guarded. So, it was nice to see that he can still have relaxed moments.


We have talked about Dean’s relationship with his father and his relationship with Jack, but we should talk about his relationship with his mother, Mary. Mary and Dean’s relationship has been at times strained and emotional, but on the other side of this is the unconditional love between a mother and son. Dean lost his mother when he was a young boy, and seeing his raw emotion after losing her again as an adult was heartbreaking to say the least. Jensen’s portrayal of Dean is always amazing, but in the moments after finding Mary’s lifeless body it really hits home for him, and for us as viewers, how great a loss this was and Jensen played it with subtle sadness.

Image courtesy of ‘Supernatural’


My favorite Dean moment from season 14 is when he was willing to sacrifice himself by getting in the box to spend eternity with Michael. Dean makes the hard choice and is determined to make sure that everyone he cares about is safe, even if it means him not being there. It always comes down to protecting others and his role in saving the world. He kept secrets from Sam, Castiel, and Mary because they would’ve tried to talk him out of it. What broke my heart was Dean spending time with his mom before he was planning on inhabiting the box. I can’t wait to see how the story ends for Dean and what next season has in store!

Image courtesy of ‘Supernatural’


My favorite Dean moment of season 14 came from the season finale. In true Dean fashion, he’s the one in this episode who immediately decides that he needs to be the one to take on the task of killing Jack because even Chuck has decided that he is a problem. All of that is nothing new, we’re used to seeing Dean be the one to risk his life for the greater good. But, my favorite moment was that moment that he dropped the gun and told Chuck, “No.” He decided that he couldn’t kill Jack. Even with God demanding it of him, he refuses. Even if killing Jack means that he can have his mother back, he refuses. It was a powerful moment of Dean showing love for Jack as well as disdain for higher powers manipulating him. You can see that moment of Dean realizing that he is done taking orders, and how his decision to not be toyed with anymore surprises even God himself.

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By Ali
She's a working mother of four children who spends free time writing, gaming with her fiance' Earl, and putting up with two really lazy cats. She's passionate about mental health awareness and being a better human. Current interests include Riverdale, Marvel, Supernatural, and Star Trek. You can find Ali on Twitter: @SongbirdAliWhi1
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