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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4. Dean Winchester Makes a Deal for Sam’s Life

Sam and Dean’s often tumultuous, but realistic, brotherly bond has been the key reason fans continue to tune in to the show. One of the earliest moments that demonstrates Dean’s unwavering love for his little brother comes in the finale of the second season of Supernatural.

In “All Hell Breaks Loose – Part 2”, Sam is felled during a Battle Royale set up by the Yellow-Eyed Demon. The creature, that cursed Sam when he was an infant, leaves Sam to die in Dean’s arms.

The scene puts Dean and the fans through the emotional wringer. How could this happen to the main character? How can Dean cope with the death of his ‘Sammy’?

Unable to accept the loss of his brother, Dean makes a deal with a crossroads demon. For the cost of his soul, the demon resurrects Sam. Dean is given a year to live before he will spend eternity in Hell. Dean doesn’t hesitate to take the offer.

The sacrifice sets up the third season’s central emotional conflict, but more than that drives home the extent to which the brothers will fight and sacrifice to keep each other safe. In the case of Dean, his protective nature as the older brother comes to the fore. He practically raised Sam and he refuses to give him up without a fight.

3. Dean Winchester Gets Yellow Fever

Supernatural is an entertaining show, but while it rides high on the emotions of its characters, some of its best moments—and episodes—are the comedic ones. High on the list of comic episodes is ‘Yellow Fever’, a highlight reel of Jensen Ackles’ superlative comedic talents.

While investigating a ‘ghost sickness’ overcoming the people in a small town, Dean is infected as well. The sickness leads him to fear everything. From crossing the street because he doesn’t like the look of some kids to screaming at the top of his lungs at the sight of a hidden cat, Dean is left quaking in his boots.

Since the sickness affects people who are jerks, the entire episode is a masterclass in subverting the trope of macho male leads. It’s a laugh riot because viewers never know when Dean’s dialogue is going to have us in splits. One of the best moments in the episode is when Dean high tails it out of ground zero as soon as a ghost appears. The way the scene is shot is perfection.

Bottle episodes like this one also give characters a moment to reflect on their crazy lives. Dean’s hilarious but poignant appraisal of the brothers’ hunting lives is funny because it’s true. Who actively looks for a monster to kill them? You should run!

To top it all, ‘Yellow Fever’ ends with Ackles lip-syncing “Eye of the Tiger,” a fun little behind-the-scenes moment for fans to enjoy after being on high alert for 40 plus minutes.