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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8. Dean Winchester’s Memorable Entrance

As introductions go, Dean Winchester has one of the more unexpected ones we’ve seen on television. The heroics in Dean’s future are but a distant dream in the pilot episode of Supernatural.

Dean is introduced to audiences by breaking into his brother’s apartment, getting into a fight with Sam, and only revealing himself when he gets the upper hand over Sam. His first spoken dialogue on the show? “Whoa! Easy Tiger.” Accompanied by a cheeky and infectious smile that continues to melt hearts. If that isn’t Dean, then what is?

This moment leads us to one of the most memorable sequences from the show. Dean mentions their dad has gone on a hunting trip and hasn’t returned. This cryptic piece of dialogue—that makes so much sense to the brothers but not yet to the audience—is the launchpad for the rest of the show, and fans are sucked into the lives of the Winchester family for 15 more years.

From the get-go, it seemed like Ackles had a complete understanding of the character—nothing Dean does in that first episode can be refuted by fans who’ve been with the show ever since. The ability to be so true to a character that was essentially cemented in his opening scene is astounding, and Ackles has done the role proud.

7. Dean Winchester Needs Sam to ‘Fight those Fairies’

In Season 6’s ‘Clap Your Hands if You Believe’, Dean and Sam find themselves investigating alien abductions—but this being Supernatural, the culprits are exposed as being more down to Earth, albeit magical.

Having been ‘abducted’ by the aliens, Dean continues to look for answers but finds himself being followed by a suspicious character. He turns through alleyways and gets a jump on the guy, only for it to turn out to be someone completely innocent. Oops.

Of course, this leads to Dean being arrested. It’s nothing he hasn’t handled before, but there’s a case to be solved so he shouts some final instructions to Sam before being taken away. “You fight those fairies, Sam!” Cue a commercial break because every viewers’ laughter will drown out the next scene.

Ackles’ moments of humor on the show are so well-timed and enunciated that one can forget that Supernatural was meant to be a horror story. And what makes this scene even funnier is that Dean is completely serious in his request since he’s made a breakthrough in the case and he needs Sam to do the work while he’s incarcerated.

But for everyone watching—including the arresting officer—seeing a man randomly scream about fighting fairies is confusing and hilarious.

Considering that this episode takes place during a terrible time in the Winchesters’ lives—Sam is soulless, and completely lacking in empathy, which puts Dean in a terrible position—these bright sparks of humor from Dean are a much-needed balm both for him and the viewers.