Supernatural: 15 best Dean Winchester moments, ranked

12. Dean Winchester Refuses to Give Up on Castiel

Dean and Castiel (Misha Collins) have a long-standing friendship beloved by fans. They haven’t always seen eye to eye, but Cas is family for the brothers.

When, in Supernatural Season 8, Cas was led down a dark path by a fellow Angel, he turned against the Winchesters. In ‘Goodbye Stranger’, Cas rehearsed killing Dean in simulations over and over to grab the demon tablet from him.

Once the chance to kill Dean presents itself, Cas seems close to succeeding. But Dean’s plaintive pleas save his life. During the 15 seasons of the show, we’ve seen that Dean Winchester is willing to take quite a beating from the people he loves because, in the end, he’s always able to snap them out of whatever’s making them hurt him.

With Cas looming over him with a fist and the angel blade, Dean reminds him that ‘this isn’t you’ and that the Winchester brothers need him; Cas is their family.

Cas finally relents, healing Dean and even apologizing for hurting him. The show’s writers never shy away from how much faith Dean has in the people closest to him. It’s no wonder ‘Destiel’ is such a huge favorite among fans. They’ve gone through hell—or rather purgatory—and back and they remain friends and brothers to this day.

11. Young Dean Winchester Goes Back to Hunting for Sam

The key to the success of Supernatural is Sam and Dean’s relationship. Despite being set in a fantastical world, the bond between the two brothers grounds the show emotionally.

While we see plenty of these instances between adult Sam and Dean, one of the most heartbreaking moments is from a flashback. Young Dean always grated against the hunting life that his father John Winchester (Jeffrey Dean Morgan) dragged the boys into.

In ‘Bad Boys’, we learn that young Dean once had to steal food to feed his brother and ended up being sent to a boys’ home. The owner gives Dean a permanent spot for him to stay and this proves to be a more stable environment for the young boy. Dean surprisingly excels at school, makes friends, and plans on a future that doesn’t involve hunting.

When he falls for a girl his age, Dean makes the decision to remain in the small town. But the moment John returns, with little Sammy waiting eagerly for his brother, Dean turns away from the life he so desperately wants and leaves in the Impala.

As if young Dean’s decision isn’t heart-wrenching enough, older Dean lies to Sam about why he left. Not wanting Sam to feel guilty for ruining Dean’s chance at living a normal life, Dean jokes that he couldn’t wait to get out of this place.