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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10. Dean Winchester Gives up Lisa and Ben

The sixth season of Supernatural was a tough one. Creator Eric Kripke had a five-year plan, but the show was greenlit for a new season, which eventually gave the Winchesters another decade of life.

While the season fumbled along, one constant was Dean hanging onto the domestic happiness he’d found with Lisa Braedon (Cindy Sampson) and her son Ben (Nicholas Elia). Lisa and Dean’s relationship had been set up way back in the third season, and when Dean followed through on his promise to give up hunting if he lost Sam, the person he turned to was Lisa.

Ben loved Dean like a father and Lisa was willing to put up with his comings and goings. Throughout the season, Lisa remained a pillar of support for Dean.

Unfortunately, you can leave the hunting life, but it doesn’t leave you. Dean tries his best to protect Lisa and Ben, eventually breaking off his relationship with them. Despite this, Lisa and Ben are almost killed, leaving Dean with no choice. In ‘Let It Bleed’, he asks Castiel to erase their memories of him to protect them from his day job.

His last interaction with them sees him apologizing for ‘crashing his car’ into them. And with that, Dean bravely closes the door on his longest-lasting relationship.

9. Dean Winchester and Death Share a Pizza

Only on Supernatural would a character enter a diner and meet the living personification of death, and no one would bat an eyelid at this occurrence.

While the exchange between Dean and Julian Richings’ Death isn’t a match for The Seventh Seal, it’s Dean’s ability to have a conversation at all that’s impressive. Ackles plays Dean as understandably terrified but also opportunistic.

It’s hilarious that we can see Dean chomping on pizza during the discussion. Death is calm and nonchalant, only losing his temper when Dean’s inflated sense of self gets annoying. In Dean’s defense, the world rests on his and Sam’s shoulders, so he’s allowed to believe he’s important.

Dean is lucky to be alive because Death needs his help to end Lucifer’s control over him. Dean plays his cards right—he’s eager to save the world, yet he’s curious about the being in front of him as well.

Dean walks away with what he needs, but with the promise that he won’t stop Sam from becoming Lucifer. As we all know, Dean tries his best to do exactly that, but fails.

Death’s warning that Dean ‘can’t cheat death’ has become an unspoken joke on the show. The boys have died innumerable times and Dean, in fact, goes on to kill Death when he tries to make the brothers murder each other.