Supernatural: 15 best Dean Winchester moments, ranked

Jensen Ackles as Dean Winchester on Supernatural
Jensen Ackles as Dean Winchester on Supernatural /
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14. Dean Winchester Befriends Benny the Vampire

If there’s one thing we know about the Winchester brothers, it’s that they hate the monsters they hunt. Vampires, werewolves, and demons have no redeeming qualities in the Winchesters’ eyes. While the brothers’ outlook has mellowed over the years, back in Supernatural Season 8, there was no love lost between Dean and the monsters.

All that changed when Dean was trapped in Purgatory. Fighting to survive on his own, Dean got a helping hand from Benny the Vampire (Ty Olsson). Benny and Dean’s friendship, though short-lived, proved how much Dean had grown from his single-minded mission as a hunter.

The two became blood brothers and Dean took several chances to bring Benny back to the real world. Dean later fought tooth and nail to clear Benny’s name, even going as far as to clash with Sam about Benny’s innocence.

In the end, Benny was unable to fit into the real world and Dean had to make the ultimate sacrifice play, kill Benny and send him back to Purgatory. At least Dean allowed Benny to go out on his own terms.

Dean’s closeness to Benny has come up several times over the course of the past few Supernatural seasons, and it’s evident that Dean still struggles with this immense loss.

13. Dean Winchester Turns Down Michael

In Season 5 of Supernatural, Lucifer’s rise could be stopped by only one person, the archangel Michael. While Lucifer’s true vessel was Sam, Michael’s was Dean.

When his brother Sam and half-brother Adam (Jake Abel) is captured by the evil the Angel Zachariah (Kurt Fuller), Dean must decide—agree to become Michael’s vessel or watch his brothers die. With no other option, Dean accepts Zachariah’s offer.

Now, the problem with becoming a divine vessel is that the human is pretty much toast when the being leaves the host body. The rules have been bent a little over the course of the show, but at the time, Dean was sentencing himself to death.

But he’s smarter than he looks. With a sneaky little wink to Sam, Dean gets Zachariah close enough to stab him with the Angel blade. As Michael descends to Earth, Dean grabs injured Sam and they rush out of Zachariah’s hideout.

Unfortunately—and this is the reason the moment is so low on our list—Dean fails to grab hold of Adam on his way out. Instead, Adam is trapped in the room and forced to take Dean’s place as Michael’s host.

But you can tell Dean is despondent by what’s happened. The look of horror and loss is another example of Ackles’ superb acting abilities.