Top 10 Dean Winchester Moments That Made Us Want to Give Him a Hug
#10: When He Was Slowly Losing His Memory
Top 20 Funniest Dean Winchester Moments on Supernatural
Memory loss is a common storyline in dramas for a reason: it’s horribly sad. Combine this with Jensen Ackles’ raw acting talent, and now we’re all staring at the screen looking like the Face Holding Back Tears emoji. Dean begins the episode not remembering the last night or knowing how he woke up in the woods. Things only get worse from there. He can’t remember the case they’re working on, people he should recognize, or even how to drive. It’s all the product of a hex from a witch, and it is quickly taking its toll. Eventually, Dean ends up in front of the mirror, repeating his own name and those of the people he loves… and then, just like that, those are gone too.
#9: When He Went to Purgatory
Top 10 Funniest Dean Winchester Moments on Supernatural
When Hell and Heaven were feeling a little been-there-done-that, the next logical place to pay a visit to was obviously Purgatory. Dean and Cas get transported after killing head chief Leviathan, Dick Roman. Even the worst classes feel endurable with a friend by your side but, unfortunately, Dean and Cas get separated, and Dean spends a whole year trying to track him down. After fighting for your survival nearly every moment and for such a long time, it’s a miracle Dean is as level-headed as he is when he’s reunited with the angel, who, it’s revealed, took off in order to protect him. All that, and they still don’t return home together.
#8: When Bobby Died
Top 10 Best Sam Winchester Moments on Supernatural
Of course, this was a moment that gutted both brothers, but there’s something to be said about the father role Bobby played to Dean more than he did to Sam. Sam always had his older brother to look to for advice and support, but Dean’s older mentor figure was always Bobby. We’d had a few Bobby scares prior to season 7’s “Death’s Door”, but the longer the episode went on, the more nervous we got. The sheer panic Sam and Dean erupt into after he’s first injured is not felt by them alone, we’ll say that much. Bobby is still hovering around for a few episodes afterward (because no one in “Supernatural” is truly gone), but the grief the brothers endure is completely palpable.
#7: When He Bore the Mark of Cain
Top 10 Sam & Dean Bromance Moments on Supernatural
The Mark of Cain, also known as The Darkness or the first curse, has corrupted many more powerful than Dean. The poor guy never stood a chance. But, options aren’t exactly plentiful when it comes to ridding Hell of Abaddon, a Knight who’s given Crowley the boot. After Dean manages to kill her with the first blade, it’s obvious something more is going on with him. He becomes straight-up bloodthirsty. This doesn’t last for too long since he’s eventually killed by Metatron but, wouldn’t you know it, the Mark brings him back to life with one teensy contingency. Can this man catch his breath for one damn second, please?
#6: Sam’s Sacrifice
Top 10 Umbrella Academy Moments That Made Us Cry
Season 5’s ending is one of the most difficult to digest. And the lead-up to get there is no picnic either. Dean and Sam learn they’re meant to be used as vessels for a fight between Michael and Lucifer. They’ve pretty much started the apocalypse and there are few moves left to make. During the fated confrontation, Castiel and Bobby are killed, and Dean is badly battered – like, we can’t believe he survived at all, badly battered. If that didn’t make us want to put a blanket over him and bring him a cup of tea, the aftermath certainly did. Dean falls into despondency without his brother. He fulfills his promise of moving on, but it’s obvious he’s a shell of who he once was.
#5: When He Died (For Good This Time)
Top 10 Simpsons Moments That Made Fans Rage Quit
It’s not so much the dying part that gets us here. After all, we’ve seen Dean die countless times by this point. Plus, death finally afforded the elder brother the peace we’d wanted for him since the very beginning of the show. Just him, Baby, and the open road for that little while... That’s not a bad afterlife. While his death certainly hurt Sam (and us) more than him, what always gets us is his goodbye speech. After everything the brothers have been through together, how could a piece of rebar be the thing that does him in? Dean deserved to enjoy victory, and life on earth with his brother just a little longer.
#4: After Mary Died
Top 10 Saddest Supernatural Moments
This is the event that pretty much kicked off Dean’s trajectory of hardship and tragedy. Not only did he have to mourn his mom at such a young age, his dad was never the same either. Few versions of Dean deserve a bigger hug than his kid self, who was overcome with grief and forced to grow up too fast. The severe toll this all took on him is no clearer than the pure awe on his face when Mary is brought back in season 11. The only thing worse than losing her once is losing her a second time.
#3: When He Lost Castiel
Top 10 Times Dean & Castiel from Supernatural Were BFF Goals
As with many of the “Supernatural” characters, Castiel has died plenty of times. Whenever Dean is around to witness it, the clear horror he expresses never fails to tug at our heartstrings. The season 12 finale stands out for a few reasons. Not only were we lured into a false sense of security before they ripped the bandaid off, but Dean and Sam would lose their mom to the portal that night too. And then there’s everybody’s favorite moment in season 15. After Cas tells Dean he loves him, The Empty claims his life. Where we usually see Dean on edge and livid after Cas is gone, this time, he just looks really broken.
#2: Hell
Top 10 WORST Hell's Kitchen Contestants
Seeing Dean getting ripped into by Hell Hounds is a moment from our first watchthrough of the show that we’ll just never forget. We were desperately hoping the boys would have found a way out before Dean’s time was up, but then it cuts to him suspended by chains and we have never felt our hearts sink faster. Living through the entire ordeal is one thing, but coming back to the living world and remembering those years of torture is a whole other level of pain. Coupled with Jensen Ackles’ performance, here, we turn into a puddle every time we watch this scene. No one deserves to have this kind of weight and trauma on their conscience, but especially not Dean.
#1: When He Lost Sam
Top 20 Sitcom Moments That Made Us Happy Cry
Dean’s primary motive has always been one thing and one thing only: protecting his little brother. We can almost commiserate with him when he’s so distraught that he refuses to bury Sam’s body and sells his soul to get him back. This wouldn’t be the only time he went to extreme lengths to save Sam, but it’s the one that feels most dire. These two are constantly sacrificing for one another but it always feels worse when Dean is the one to lose his brother. Not only does he have to deal with the grief, but also the heavy burden of failure to protect the one person he always swore he would. Which moment warranted the biggest hug? Let us know in the comments.
