With only one season left of Supernatural, fans are reminiscing about the "road so far," remembering all of the feels Sam and Dean Winchester have delivered over the past 14 years. It's almost overwhelming to think about.
Despite Dean presenting such a hard shell to the outside world, his vulnerability has been exposed every single season, sometimes so raw and poignantly it moves us to tears. Whether he's meant to or not, and whether it was out of his own terrible deeds or the sorrows he's experienced, Dean Winchester has broken our hearts several times over the years. We're still recovering from some of these moments.
10 He Offed Sam's Friend
In a moment fans are sure will haunt him this season, Dean Winchester struck a blow to a mostly benign monster who only hurt people to feed her own child. She also happened to be a friend of Sam's, which made the offing an even more heinous act that broke our hearts.
Her son vowed revenge, but it's been years since he did and the show only has one season left to go. Fans are speculating that by now, the boy, Jacob Pond, has grown, gotten strong and is ready to fight a Winchester brother in honor of his mother's passing. We don't doubt that Dean would do the same.
9 He Cried At John's Grave
Dean is always going on about how he refuses to get emotional. No touchy-feely for this hunter, thanks. Yet every time you turn around, there he is with the waterworks or some emotional line that drives a stake right through our hearts, like the time he poured out his feelings to his father's grave.
Dean demanded, "Why is it my job to save these people? Why do I have to be some kind of hero? What about us? Why do we have to sacrifice everything, Dad?" As tears pour down his face and we realize he's saying what he could never ask while his father was alive, we weep with him.
8 When He Was Offed Over And Over Again
In many ways, the 11th episode of season three, "Mystery Spot," is hilarious. It dealt with Dean being offed in new ways, over and over again, as Sam relived the experience. Of course, it turned out to be a trick courtesy of the trickster god, AKA Gabriel, as a warning to Sam, while Dean didn't believe that he and his brother were living in this Groundhog Day cycle. Even so, he expired over 100 times.
It was ridiculously too much to handle and we got lucky that some of the moments were so funny because it was so difficult to see Dean offed again and again.
7 When Metatron Offed Him
The time Metatron offed Dean by stabbing him with his angel blade ripped us to pieces. Not only did Metatron do this so easily, he did it right in front of Sam, who had to witness Dean not only expire but also become the Knight of Hell.
Dean had a hard time dealing with the Mark of Cain the entire season and we knew something bad was going to come of it, but he went ahead and broke our hearts double-time as he left Sam to go party hard with Crowley, leaving poor Sammy to search for his big brother. Seeing Dean completely careless about Sammy was just too much.
6 When The Hellhounds Got Him
The first time we lost Dean was one of the hardest. He'd already sold his soul to save Sam's life, and as he waited for the hellhounds to come for him we waited with bated breath, sure that he'd find some way out of it. He didn't, and that was the end of the third season.
To add insult to serious injury, we learn that not only was Dean in Hell for forty years instead of four months, but he also became one of the minions who tortured other souls while trapped in Hell. Had we known what else was in store for Dean down the road, perhaps it wouldn't have broken our hearts so hard.
5 He Left Lisa And Ben
When Dean finally found happiness with his ex Lisa and her son, Ben, the spitting image of himself, fans had a bittersweet response. He'd lost Sammy, but he was finally enjoying a normal life...until the djinn proved that he couldn't even have that.
It wasn't just the loss of Squirrel's happiness that got us in the gut, but how he had to leave his newfound family. Dean had to erase Lisa and Ben's memories of him to keep them safe, eliminating many of the best moments of his life from their minds. It was one of his most heartbreaking sacrifices and remains so to this day.
4 He Left Adam In The Pit
Another harrowing decision that Dean made, along with his brother, Sam, was to simply leave their younger half-brother, Adam, in the pit with Lucifer and Michael to rot. Had it been either of them, they would have sought after one another, but Adam hasn't even been mentioned since.
Jensen Ackles and Jared Padalecki have joked about this on comic con panels, but in reality, fans believe it's something that will have to be addressed this final season. After all of that time spent in the pit, Adam likely isn't going to be very friendly toward his estranged brothers, either.
3 When Castiel Almost Killed Him
When Naomi brainwashed Castiel to go after Dean, it was almost too much for our TV screens. It was bad enough that Cass had already slain multiple duplicates of Dean in training for the moment a la The Prestige, but watching the angel beat Dean up like that while Dean simply refused to retaliate was one of the worst things we've ever witnessed on the show.
It proved Dean's devotion to the angel, and it became a key point in their timeline Dean/Cas shippers, or "Destiel" shippers, particularly when Dean pleaded, "Please," to his friend. Affirmation of this 'ship is another final season plot point many fans hope to see.
2 When He Went To Heaven
Dean has given us the feels more times than we can count, particularly when it comes to how he deals with loss. Whether it was his father, his brother, Bobby, Charlie or anyone else close to him, Dean has always taken us with him, helping us feel his pain.
When he and Sammy were shot and sent to Heaven, it was even more affecting because we witnessed what Heaven was to him: Childhood moments spent with Sammy. It still chokes us up to think about it, especially since Sam's Heaven was made up of moments away from his family, which is even more heartbreaking.
1 He Kept Castiel's Coat
When we lost Castiel to the worst decisions made with the best intentions, it really did appear as if he were gone for good. At the beginning of season seven, after Leviathans take control of Castiel, his vessel completely disintegrates, leaving his trademark trench coat behind.
When Dean folded it up like a soldier's flag, there wasn't a dry eye in the audience. Ackles and Padalecki have both poked fun of the episode, which has been compared to the equally moving one at the end of the film Brokeback Mountain, but it remains one of the most heartbreaking moments in the history of the show.