January 24th marks the birthday of one of T.V.s best characters, Dean Winchester, played by the incomparable Jensen Ackles. While Supernatural ended its record-breaking 15-year run last November, we would be remiss if we didn’t celebrate this famed Winchester brother.

Warning! Spoilers from here on out.

By now, we know that Dean met his untimely end in the series final, Carry On (15×20), so this would have been his 42nd birthday. His death is still very fresh in our minds, but we will carry on his memory by reminiscing on my ten favorite Dean Winchester moments. This is not a comprehensive list because over the course of 15 years, Dean has made us laugh and cry during every hunt and every world-saving event. There are gems in every episode, but here are the ones that continue to stand out. These are moments when Dean showed his vulnerability and his beautiful humanity, so be prepared.  

1. Dean Remembering His Family (Regarding Dean 12×11)
Top 10 Favorite Dean Winchester Moments

Supernatural –“Regarding Dean”– SN1211b_0222.jpg — Pictured: Jensen Ackles as Dean — Photo: Dean Buscher/The CW — © 2017 The CW Network, LLC. All Rights Reserved

Arguably one of Dean’s most heartbreaking moments is when he struggled to remember the names of his family and his best friend, Castiel (Misha Collins). In Regarding Dean, Dean is struck with a curse that slowly erases his memory. As Sam (Jared Padalecki) and Rowena (Ruth Connell) try to find a way to reverse the spell, Dean does his best to be optimistic. Soon it becomes clear that there might not be a cure and that he will lose all memory of himself and his loved ones. Alone in a restroom, Dean says the names of his family out loud until he finally admits that he can no longer remember. This scene has been lauded by many as depicting the true struggle of those who suffer from Alzheimer’s and similar illnesses. 

2. Dean Remembers Hell (Heaven and Hell 04×10)

After Dean is pulled from Hell by Castiel, he claims that he no longer remembers what happened while he was there. Unfortunately, in true Dean fashion, he had buried those memories deep within. It wasn’t until after the events with Anna (Julie McNiven), Uriel (Robert Wisdom), and Cas that Dean opens up to Sam. We learn that Dean spent 30 years in Hell and for all those years he held out on torturing other souls, until he finally gave in. The pain of what he did to those souls is too much for him to bear, but he eventually tells Sam everything.

3. Dean Really Likes Cowboys (Tombstone 13×06)
Top 10 Favorite Dean Winchester Moments

Supernatural — “Tombstone” — Image Number: SN1306a_0215b.jpg — Pictured (L-R): Misha Collins as Castiel and Jensen Ackles as Dean — Photo: Bettina Strauss/The CW — © 2017 The CW Network, LLC All Rights Reserved.

It is no secret that Dean is a fan of the Wild West and stories about famous gunfighters, outlaws and lawmen. In Tombstone, we get to see just how much he loves those stories. Following Cas’s unexpected resurrection, Dean, Sam, Cas and Jack head to Dodge City for a case. They stay at a hotel that is heavily influenced by Dodge City’s Wild West roots. The sheer joy that Dean feels as he looks at old pictures of gunfighters is endearing and we can’t help but smile at his enthusiasm to tell everyone about what he knows. It is one of the rare moments where Dean gets to show us this side of him.

4. Dean Recruits Castiel (Lucifer Rising 04×22)

At the end of Season 4, Sam and Dean try to divert the Apocalypse by stopping Lilith (Katherine Boecher) from opening the last seal and releasing Lucifer. Dean is captured by the angel Zachariah (Kurt Fuller) who confesses that both the angels and the demons want the Apocalypse to happening so that they can finally settle their millennia-long grudge match. With humanity caught in the middle of this epic fight, Dean tries to persuade Castiel to help him stop Sam from killing Lilith. In a heartfelt speech, Dean tells Cas that he will take the pain and the guilt of living in their world as is if it means having freedom. When Castiel eventually joins Dean, it sets him on the path of rebellion and unwavering loyalty that lasts until the final episodes of the show. This moment shows the true power that Dean has as a representative of humanity.

RELATED: A Farewell to Supernatural

5. Dean Will Always Choose Sam (Sacrifice 08×23)
Top 10 Favorite Dean Winchester Moments

Supernatural — “Sacrifice” — Image SN823b_0169 — Pictured (L-R): Jensen Ackles as Dean and Jared Padalecki as Sam — Credit: Diyah Pera/The CW — © 2013 The CW Network. All Rights Reserved

In Season 8, Sam and Dean discover a way to close the gates of Hell by completing three trials as outline in the Demon Tablet. Sam takes on this burden and slowly we see Sam deteriorate as the trials take their toll on him. In Sacrifice, Sam is just about to complete the Third Trial when Dean stops him. Sam is so desperate to close the gates that he accepts that he is going to die, but Dean, ever the protective one, refuses to let Sam end his life to close the gates. The brothers share a powerful moment in which Sam confesses that he felt guilty for always letting Dean down and that seeing Dean put his faith and trust in others hurt him deeply. Dean begs Sam to understand that he would never put anyone else before him. It’s a moment that solidifies the love these two brothers have for each other.

6. Dean Has Lisa and Ben’s Memories Wiped (Let it Bleed 06×21)

Lisa Braeden (Cindy Sampson) and Ben Braeden (Nicholas Elia) are a mother and son whom Dean lived with between Seasons 5 and 6 after Sam is thrown into the cage with the Archangels Michael and Lucifer. This would be the only time that Dean tries to live a normal, non-Hunter life. Unfortunately, the King of Hell, Crowley (Mark Sheppard), uses their relationship to his advantage in Let it Bleed when he sends his demons to kidnap Lisa and Ben. Dean mounts a rescue and Lisa is severely injured in the fight. At the hospital, Dean tries to talk to Ben about what happened, but he can see that his lifestyle has hurt the ones he loves. He asks Cas to wipe Lisa and Ben’s memories of him because despite how much he loved Lisa, her safety was more important than anything else.

7. Dean and Cas in Purgatory (The Trap 15×09)
Top 10 Favorite Dean Winchester Moments

Supernatural — “The Trap” — Image Number: SN1509B_0108bc.jpg — Pictured (L-R): Misha Collins as Castiel and Jensen Ackles as Dean — Photo: Colin Bentley/The CW — © 2020 The CW Network, LLC. All Rights Reserved.

Season 15 pits the Winchesters, Cas and Jack against God (Rob Benedict). After a falling out between Cas and Dean, they are reunited and sent back to Purgatory, a place they survived years before. When they are attacked and separated, Dean attempts to get a hold of Cas by praying to him. It is in this open and honest prayer that Dean talks about his anger and stubbornness in refusing to admit that he was wrong. He forgives Cas and hopes that his forgiveness is enough. This is the moment in which Dean fully addresses his deep-seeded anger issues but more importantly, this is when Dean truly realizes how important Castiel is to him. 

8. Dean Evaluates Jack Using Cake (Peace of Mind 14×15)

With the introduction of Jack (Alexander Calvert), the son of Lucifer and Kelly Kline, in Season 13 we got to see the paternal side of Dean. By Season 14, Jack had almost completely burnt out his soul so when Dean tells Jack to try either a Devil’s Food Cake or an Angel Food Cake for the first time, he is very interested in what Jack chooses. The sheer concern on Dean’s face when Jack contemplates choosing the Devil’s Food Cake is hilarious, but his audible sigh of relief when Jack chooses Angel Food Cake is downright hysterical. Only Dean Winchester would use small little cakes to see if a Nephilim is going to be a danger to him.

9. Everything Scares Dean (Yellow Fever 04×06)

We all know that Dean is rarely scared of anything, but in Yellow Fever that all changes. After being infected with an illness that causes anxiety and eventually ends in death, Dean must deal with fearing everything. Of course, we will never forget Dean’s shrieking at the sight of a cat jumping out of a locker because that is comedic gold. Dean throughout the whole episode plays it fun, which is a huge departure from the very serious and dramatic character that he is. The bonus is the end credits when Jensen performs “Eye of the Tiger” while mostly remaining in character.

10. Dean Confronts Mary (Who We Are 12×22)
Top 10 Favorite Dean Winchester Moments

Supernatural –“Who We Are” — SN1222a_0163.jpg — Pictured (L-R): Jensen Ackles as Dean and Elizabeth Blackmore as Toni Bevell — Photo: Diyah Pera/The CW — © 2017 The CW Network, LLC. All Rights Reserved

Season 12 not only brought us the British Men of Letters arc but also the return of Mary Winchester (Samantha Smith). In Who We Are, Mary is brainwashed by the British Men of Letters and helps Ketch (David Haydn-Jones) trap Sam, Dean, and Lady Bevell (Elizabeth Blackmore) in the bunker. They are able to capture Mary and in an effort to cure her, Dean connects with her mind. There he sees Mary relieving her time with young Dean. Dean takes this moment to confront her about the choices she made that ultimately lead to her death. This is a heartbreaking scene in which Dean tells her that he loves her, but he also hates her for leaving them and for everything that happened afterward with their father and the pain and heartache that Sam had to endure. In the end, he forgives her.

RELATED: Read All of our Supernatural Recaps Here!

11. Dean Sings (Last Call 15×07)

It is no secret that Jensen Ackles has a phenomenal voice; however, Dean Winchester is a little hit or miss as shown in a few episodes where he sings karaoke with Crowley or “Night Moves” with his brother. But in Last Call, we finally get to hear Dean’s actual singing voice when he sings a duet with his friend Leo Webb (Christian Kane). Not only that, but we get to see him happy, singing in front of people at a bar with a friend. After everything that has happened in the last 15 seasons, it is moments like this that bring real joy to Dean’s life and we love to see it. It’s what he deserves.

Happy Birthday, Dean Winchester. Thank you for the laughs, the tears and for being a beautiful human soul that did everything for love.

This article was originally posted on 1/24/21


Renee Lopez
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