Supernatural: 10 Questions About Dean Winchester, Answered

The announcement of the Supernatural spin-off known as The Winchesters has brought back interest in all the main characters. In any case, there have always been questions about Sam Winchester and his brother Dean, as the sprawling 15-year run of the dark fantasy series left a lot of things up in the mix.

There are plenty of facts known about Dean that are worth recounting now that his story is set in stone, and fans can find all the answers to their most sought-after questions. For most fans, Jensen Ackles will always be known mainly as Dean Winchester, so it’s also a way for The Boys viewers to know enough about his most famous character before the actor appears in that series.

10 Who Was His Archenemy?

Dean didn’t have an official archenemy the way Sam did with Lucifer, but there were certain foes he hated more than others. All things considered, Dean’s main enemy has to be the Prince of Hell, Azazel, who was responsible for the death of his parents.

Moreover, Dean thought of Azazel as his biggest fear whenever he was afflicted by paranoia and curses, with his killing of Azazel being one of Dean’s greatest achievements. By the series’ end, Dean also started considering God as his main foe when he realized Chuck had been playing with his life the whole time.

9 Who Were His Closest Friends?

While Sam didn’t seem to have many firm friendships, Dean was the character who did have personal connections. Here, the easy winner has to be Castiel, as Dean thought of him as his best friend. In addition to the angel, Dean had a habit of forming unusual friendships.

His next closest friend has to be the vampire Benny Lafitte, whom Dean continued to think fondly of even years after passing. Dean also developed a firm friendship with Crowley when he was a demon, which continued sporadically later on as well. Another close friendship was with Charlie Bradbury, whom Dean likened as a younger sister.

8 Who Were His Major Love Interests?

Dean began the series by himself and ended his run on the show being single as well. However, he had a number of love interests in the interim, with some of them ending in trademark Supernatural tragedy. Overall, there were a few women who can be considered as Dean’s greatest loves.

Lisa Braedon was a former flame with whom Dean settled down for a year before an attack by a demon caused Dean to leave her permanently. Dean had a short-term romance with the angel Anna before she regained her grace, and wanted to settle down with Cassie Robinson in her youth but the latter couldn’t accept his role as a hunter.

7 How Many Times Did He Die?

Death was hardly the end where Winchesters were concerned, with Dean being the character to experience it the most. All in all, Dean died 111 times during the series and the series finale fittingly concluded with his demise as well.

Most of his deaths occurred in Season 3’s “Mystery Spot,” where the archangel Gabriel caused Dean to die every day. Apart from that, Dean died eight times on other occasions, with the first of these sending him to Hell. His final death was the one that stuck and Dean ascended to Heaven where he remained for eternity.

6 How Critically Acclaimed Was The Character?

Supernatural was never an awards season favorite due to it being part of the fantasy genre, but Dean is still the most acclaimed character out of the series. Jensen Ackles was nominated for a number of awards during the show’s run, with his final victory the most major one.

Ackles won the Critics’ Choice Super Awards for Best Male Actor in a Horror Series after Supernatural concluded, marking the series’ biggest award. Prior to that, the actor also won a People’s Choice Award for Best Sci-Fi/Fantasy Actor, to go with nominations at the Ewwy Awards and SFX Awards.

5 What Recurring Gags Are Associated With Him?

Dean was the designated comic relief character for Supernatural, with most of the jokes coming at his expense or due to his mannerisms. One of the longest-running gags associated with Dean was his love for pie, which he hardly ever got to eat as Sam would usually fail to buy it for him or get a bad replacement like cake.

Another similar gag was Dean’s tendency to be a big eater, with just about every episode showing him munching down food much to the annoyance of Sam. This gag was even acknowledged on the show when Dean realized he’d been able to eat without suffering stomach problems due to Chuck allowing him to.

4 How Many Big Bads Has He Killed?

Dean could easily be considered as the biggest threat for the villains in the series. He has the largest kill count of any character and was responsible for taking down the majority of the main antagonists.

By the series end, Dean had killed Big Bads including the Prince of Hell Azazel, the Seraph Zachariah, the archangels Lucifer and Michael, the monsters’ mother Eve, the Knight of Hell Abaddon, the Leviathan leader Dick Roman, and both Billie and the original Death.

3 How Many Realms Did He Visit?

Despite being a human with no powers to willingly reach different realms, Dean ended up as the most traveled being in the universe apart from Chuck. He and Charlie were the only humans to ever be in the fairies’ realm of Avalon, while Dean also visited alternate universes like the Apocalypse World and the Bad Place.

In addition to those, Dean visited the French Mistake universe to go with a number of realms that had no physical location. These included Heaven, Hell, and Purgatory, all of which Dean remained in for significant stretches of time.

2 Who Is His Immediate Family?

It’s actually pretty difficult to keep track of all the people Dean was related to, as the Winchester family and other relatives were quite a lot. In the immediate family, Dean and Sam’s parents were John and Mary Winchester, with maternal grandparents being Samuel and Deanna Campbell, and paternal grandparents Henry and Millie Winchester.

Dean also had a half-brother in Adam Milligan from his father’s side, while he had a daughter named Emma with an Amazon, who was killed shortly after when the girl tried to take his life. Finally, Dean posthumously became an uncle when Sam had a son whom he named Dean after his brother.

1 How Long Did He Live?

Spiritually, Dean was 40 years older than his age as he spent that time in Hell. In Earth years, Dean didn’t even get close to old age as he met his end when fighting vampires. Although it appeared as if Dean had died in 2020, it was a little while later.

The finale took place five years after the penultimate episode, according to Jared Padalecki, placing the timeline in 2025. By this point, Dean would have to be 46-years-old, leaving that as his final age. In Heaven, he met Sam about 25 years after his death, meaning Dean would have been 71 had he lived until then.

About The Author

Saim Cheeda
(1343 Articles Published)

Saim Cheeda is an entertainment writer covering all of Film, TV, Gaming and Books. He’s been a writer for Valnet since 2017, contributing 500+ articles for The Gamer, The Things, Game Rant, Comic Book Resources and Screen Rant. Apart from freelance writing, Saim is a lifestyle blogger, co-owning the blog 3 States Apart.

http://3statesapart.com

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