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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Jensen Ackles as Dean Winchester on Supernatural
Jensen Ackles as Dean Winchester on Supernatural /

What are the best Dean Winchester moments on Supernatural?

In the early noughties, a weekly show about demon-hunting brothers may have seemed like a bad joke, but Supernatural turned fans around swiftly with the unforgettable dynamic between its protagonists.

Dean Winchester (Jensen Ackles) and his younger brother Sam (Jared Padalecki) couldn’t be more unlike each other. Dean is brash, often uncouth, and loves hunting. Sam, on the other hand, is cerebral and has always dreamed of having a normal life.

Forget demons, ghosts, and ghouls, viewers were immediately sold on this unlikely pair and their road trip to save the world.

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Much of the show’s appeal lies with Dean—humorous and sometimes goofy, Dean is the definition of the hero with a heart of gold.

Dean has never shied away from making the tough decisions even if it mars his soul—as long as he can save the people he loves and the world, he’s ready to risk it all.

But it is Dean’s unwavering loyalty and love for his brother that has kept fans engaged for 15 seasons. There is nothing in the world that Dean Winchester wouldn’t do for his little brother and that elevates him above the stereotypes that could have shackled him.

Now that the show is ending after a 15-year long run, we look back at Dean Winchester’s greatest moments. This was a hard one for us, because not only is Dean a layered character, but he is played with effortless passion by Jensen Ackles.

Ackles has the ability to infuse Dean with great humor and immense pathos. He is talented enough to have viewers guffawing in one scene and turning into blubbering crybabies the next. So, which Supernatural favorites made it into our top 15?

15. LARP-ing Dean Winchester

Dean Winchester doesn’t often get the chance to let his hair down, but when he does, he takes that opportunity with both hands.

In ‘LARP and the Real Girl’, Sam and Dean meet up with fan-favorite supporting character Charlie (Felicia Day), one of the rare queer characters represented on the show. Charlie is a geek through and through and takes to LARPing (live-action role-playing) in this Season 8 episode, to escape the hunting life.

When LARPers end up dead, Sam and Dean are at hand to investigate. After discovering a magical world, complete with a damsel in distress who is saved by Charlie, the brothers make good on their promise to Charlie—to join her army and help her win the game.

Dean, in full Braveheart regalia, complete with war paint and lustrous wig, delivers William Wallace’s battle cry from the film with aplomb. One can tell that Dean takes every fight seriously, including fictitious ones. This fight is no different.

What sells the scene is Ackles’ dedication to reproducing the speech with the same passion and charging into battle as though he’s been transported to the 13th century. What could have been a forgettable episode is made indelible by the showrunners embracing the sillier side of Dean?