Only A Hardcore Supernatural Fan Can Answer These Dean Winchester Questions

A lot of Supernatural fans will debate who the biggest star of the show is - and with such an incredible cast, it's no wonder! However, there are only two characters who have been with the show from its pilot episode to the thirteenth season (and who will stay with the show for seasons to come): Sam and Dean Winchester. These brothers are hunters, men who have dedicated their lives to killing the things that go bump in the night, and who have saved the world more than once. They've even died in the process, but while many characters on Supernatural stay dead, Sam and Dean are just impossible to kill permanently!

Of the two, Dean is the sarcastic one, the one who loves junk food and strippers and would do anything to protect his brother and the people he loves. He's also the one who suffers the most, sometimes, and who has real hidden depths beyond his leather clad exterior. He's befriended angels and demons - especially Castiel and Crowley, and he's not only been in more realms than any other character on the show, he's also time travelled more, died more, and killed more main antagonists than anyone else.

In short - Dean Winchester is a card-carrying badass... but how well do you know him, really? Are you a Dean fan through and through, or is Sam more your speed? Take our quiz to find out!

Question 1

When was Dean born?

Neither Sam nor Dean really celebrate their birthdays on Supernatural - it's not too surprising, given that they are usually too busy saving the world... not to mention that the number of times they've been killed and resurrected, it's probably getting a little bit pointless to celebrate every single time they've come into the world! However, we have seen Dean's legal birthday, thanks to some details on the series - and some interviews where it is revealed that it is the same day as the series creator's wife!

Question 2

Where is the Men of Letters bunker where Dean lives?

For the first several seasons of Supernatural, Sam and Dean lived on the road, in their car and in sleazy motels. It's difficult to maintain a real family home when you always have to be travelling to hunt, and of course, when monsters and demons would love to know where to find you! However, they eventually discovered the Men of Letters bunker - a fortress filled with books of lore, weapons, and magical items that they can now use as a base and a real home.

Question 3

Is Dean older or younger than Sam?

Sam and Dean's relationship is the heart and soul of Supernatural - these two brothers have protected each other their whole lives. They were raised almost entirely by their father on the road, who trained them to be hunters and to continue the family business. They continue to protect each other, and are willing to do almost anything when one dies to bring them back to life - they have sacrificed everything for each other - but which is the older of the two?

Question 4

What is Dean's Mom's name?

Dean's Mom was a huge part of the series from the start - even though she died in the pilot. Slowly, her history was revealed; that she was actually raised as a hunter herself, in a family of hunters, and that the family connection to the yellow eyed demon started before she even had Sam and Dean. Then, in recent years, she was actually resurrected, as a gift to Sam and Dean from the Darkness, and has become a fan-favorite character.

Question 5

What is Dean's Dad's name?

Dean's father has also featured throughout the years on Supernatural - in the early seasons, he appeared as a living hunter, who the boys worked with. However, even after he died, that didn't stop the character from showing up from time to time. He's appeared in flashbacks, but also when Sam and Dean travelled back to the past when he and Mary first met. Who knows, he might even come back from the dead at some point too - it is Supernatural!

Question 6

Who is Dean the chosen vessel for?

There is a lot of lore in Supernatural around the concept of both angelic and demonic possession, and while demons have the ability to possess any meat suit that they happen to come across, angelic possession is a little bit different. Angels have to get permission from a human to possess their body - and even then, they can only inhabit that body for a short while before destroying it... unless the human is a true vessel, of course. Dean is the true vessel for which archangel?

Question 7

What's Dean's favorite dessert?

While Sam likes to take care of his body, and is known for his love of salads and smoothies, Dean takes a much more casual approach to his diet... and given that he's come back from death multiple times, maybe caring about saturated fat or sugar isn't a big deal! He especially loves one dessert in particular though, and always asks for it whenever they stop - even though it's a bit of a running joke in the series that he rarely gets to actually eat it!

Question 8

What's the name of Dean's half brother?

While Sam and Dean are the core brothers of the show, they actually discovered that they aren't the only Winchester boys out there. In the fourth season of Supernatural, they discovered that their father had had a relationship with another woman, and even had a son with her. This young man became a key player for a short while, although he eventually gave up his life to act as a vessel, and was trapped in the Pit with Lucifer, which (presumably) drove him insane.

Question 9

Who did Dean live with when Sam was in the Cage?

At various times in Supernatural, both Sam and Dean have attempted to live something that looks like a normal life - when the other brother was presumbed 'dead'. However, these attempts at normalcy always end up short lived. When Sam was trapped in the Cage, and had told Dean not to try and get him out again, Dean went back to a woman that he had had a few flings with in the past. The two lived together with her son for some time, until Sam returned and they went back on the road.

Question 10

Who did Dean have a child with?

Although Dean briefly thought that Lisa's son, Ben, might have been his, that turned out not to be the case. However, he did act as a father figure to Ben, and is seen as being good with kids throughout the series... and did, once, actually have a child of his own. However, this happened when he had a one night stand with a 'monster', and the child grew up rapidly before coming after her father to kill him - and Sam killed her.

Question 11

What biblical weapon did Dean bear on his arm?

As the series continues, it gets more and more biblical. Angels and demons are introduced, as well as Heaven, Hell, and even God himself. Other biblical stories started to be introduced in the series as well, from Eve to the Four Horsemen of the Apocalypse, and finally, to one of the oldest stories of brothers in the Bible. This one came about when Dean was trying to defeat Abbadon, and took a biblical curse onto his body in order to do so.

Question 12

What happened when Dean had the Mark removed?

When Dean bore the Mark of Cain, it was revealed that this was not just a powerful weapon to use against evil... it was also a curse, that would eventually destroy him. He and Sam did find a way to get the Mark of Cain removed, in the end, but saving Dean from it ended up having terrible consequences for the world (not the first time that's happened, though...) as the Mark is also 'a lock and a key' to what evil that was released?

Question 13

What is Dean allergic to?

Only the most eagle eyed viewers will be able to answer this one - although it has come up in the series! In the episode 'Man's Best Friend With Benefits', a mild allergy that Dean has is revealed by something as small as a sneeze... although thankfully, this isn't an allergy that really impacts his life - it's not as though he's allergic to beer or pie! However, it does occasionally make this Winchester sneeze when working on specific cases.

Question 14

What kind of car does Dean drive?

Dean's car is practically a character in its own right, even though it's definitely not a human one! This classic muscle car originally belonged to the boys' father, John Winchester, before Dean inherited it. He's worked on the car extensively, and never lets Sam drive if he can help it. This car even served as a kind of home to the Winchester boys when they were still living on the road, and before they found the Men of Letters bunker.

Question 15

What food did Dean crave most in Purgatory?

Dean's love of food is well known to fans of the series, but it's not just pie that he craves! There's also a greasy, savory treat that Dean is known to eat every chance he gets - even though Sam keeps telling him how bad it is for him. When Dean was trapped in Purgatory, he dreamed about getting home again, and said that the first food he would eat when he finally came back to Earth would be this.

Question 16

Which Actor's movies is Dean a huge fan of?

While Sam might be a bit of a geek, and a lover of the Harry Potter and Lord of the Rings franchises, Dean is a man of simpler tastes. He's not really into books or TV shows, and would rather go to a bar for a beer than watch TV or movies at home. Despite this, he is a huge fan of one particular star of classic movies, and as Sam says, he can recite every single one of this actor's movies, line for line.

Question 17

What is Dean's favorite genre of music?

As well as loving classic Westerns, Dean is known for loving a very particular genre of music - which he listens to in the car, thanks to a cardboard box full of actual cassette tapes! When he died, and Sam got the car and installed an iPod jack so that they could listen to some more modern music, Dean was livid, and threw it away as soon as he was resurrected. Nope, there is only one genre of music that works for Dean!

Question 18

What does Dean have a fear of?

Dean Winchester isn't afraid of much - as a hunter, and a hunter as famous as he is, Dean is the thing that monsters fear... not the other way around! However, that doesn't mean that he's completely fearless... he may be fine with vampires, demons, monsters, and even the depths of Hell itself, but he has one very prosaic fear that impacts his life - and that has been revealed in the show more than once. What is it that Dean is afraid of?

Question 19

What is the name of Dean's ex?

Although Dean isn't known for his long term relationships, preferring one night stands (that make more sense with the job, anyway), he does have at least one serious girlfriend. It's established that he dated this woman before the series began, and that they even got serious enough that he revealed to her that he was a hunter... at which point, she decided that he was completely insane, and left him. She does pop up later in the series though, although they obviously don't get back together.

Question 20

What is the name of the vamp Dean befriended in purgatory?

Dean was transported to Purgatory, a Hell for monsters, after he killed the leader of the Leviathans... and while there, he had to struggle to survive every single day. He wasn't entirely alone, though, as he met the soul of a vampire, who was willing to help Dean find a way out that he knew of... as long as Dean was willing to bring him back to life as payment. The two ended up forming a strong friendship, that lasted when they were both back on earth.

Question 21

Why did Dean become a demon?

As well as having died and been resurrected more than once, both Sam and Dean have also gone through some other near-death experiences... including the loss of their souls. Sam lost his soul when he was brought back from the Cage without it, while Dean slowly turned into a demon thanks to the use of an incredibly powerful magical item, that turned out to be cursed - and when Dean died, it resurrected him as a demon, or a 'deanmon', to fans.

Question 22

Who was Dean named after?

For most of the series, it is made clear that Sam and Dean believe that the only family they have is each other - and of course, their father at the start. However, as time goes by, fans learned about the extended family of hunters on the Winchester brothers' maternal side, as Mary Winchester's history was revealed to them thanks to some time travelling adventures. On one of these, they met a woman, Deanna, that Dean is named after. What is her relationship to him?

Question 23

Which of these monsters has Dean become?

As if dying multiple times, losing his brother multiple times, being trapped in Purgatory, turned into a demon, and being tortured in Hell wasn't enough, poor Dean Winchester has also been turned into one of the monsters that he hunts. He was turned while doing his usual work, but thankfully, he didn't have to stay a monster for long - as it turned out that the Campbell family (his mother's family) had developed a cure that could be used on him.

Question 24

Which of the Horsemen did Dean kill?

In season 5 of the series, Supernatural introduced the Four Horsemen of the Apocalypse, biblical figures with powerful rings, updated for the modern age. Each brought their own specific power with them wherever they went, of course, but instead of the horses that they used to ride, they now each have a car of the appropriate color, for example. Despite their power, Dean actually killed the oldest and most powerful of the Horsemen with their own weapon... but only after striking several bargains with him.

Question 25

Which of these is a high school Dean attended?

When Sam and Dean were growing up, it wasn't just hunting that they learned - they also had to go to school! Obviously, Sam even managed to do well enough to go on to university, and Dean also got a GED eventually... but it wasn't easy, especially when they moved around so much. In the season 4 episode 'After School Special', fans got to see a little bit about their high school experience, as well as the name of one high school they attended.

Question 26

Dean is the first human to set foot where?

Dean Winchester has managed to travel to realms that most people wouldn't even know existed. He has been to legendary places, he has travelled through time, he has walked in Heaven (and in the parts of Heaven where human souls don't usually end up) and he's been tortured in Hell. He's died so many times that it must seem like he's explored every possible afterlife, and yet, there are still places he is discovering - where was the place he was told he was the first human to set foot in?

Question 27

Crowley nicknamed Dean what?

Crowley may be a demon - and one of the most powerful demons in Hell, at that! - but he's got an interesting relationship with the Winchester brothers. He may have started out as an enemy to the hunters, but he's become something of a friend and ally, even if no one really wants to admit that the world's best hunters are friends with the King of Hell... Crowley even has a nickname for the boys - what's his nickname for Dean?

Question 28

When did Dean make his first sawed off shotgun?

Dean and Sam are known for having a huge arsenal of weapons - and it just seems to keep growing each season! They have added mystical and incredibly powerful artifacts to their existing pile of lore books and rock salt, but they've also got plenty of good ol fashioned guns at their disposal... and the boys have been learning how to use guns and knives since they were kids! Dean has even revealed the age at which he made his first sawed off shotgun...

Question 29

What does Dean have tattooed on his chest?

It often seems as though a guy with the personality that Dean has would have more tattoos - and originally, the character was meant to have quite a few! However, Dean only has one (that has been revealed in the series, anyway!) - which is on his chest. Sam has the same mark, and the tattoo isn't just for looks... these are tattoos of mystical symbols that help keep Sam and Dean safe when they are out dealing with monsters...

Question 30

What color are Dean's eyes?

When Dean became a demon, his eyes turned that same black that all demons have... however, most of the time, he looks very different! Fans have even compared Dean (and Jensen Ackles, the actor who plays him) to a Disney Princess because of his big beautiful eys - and with so many heartwrenching scenes in the series, we've had plenty of opportunities to see those eyes in close up, welling with tears at the latest tragedy to befall the Winchesters.

Question 31

How does Dean take his coffee?

Dean would undoubtedly rather have a beer in hand, but obviously, he drinks a lot of coffee... it's a tough life, staying up to battle evil, and then having to be awake (and driving) again in the morning to do it all again! Because of this, we've seen on the show how both Sam and Dean take their coffee, although it's only the most dedicated fans who would be able to remember whether Dean wants cream, sugar, or coffee as black as a demon's eyes...

Question 32

What's Dean's go-to move in rock, paper, scissors?

Although fighting evil and saving the world seems like it would be serious business, Sam and Dean Winchester don't spend too much time taking it seriously. Maybe after doing it for so long, it's just difficult to be very grim about it all the time... so they have some fun, they crack jokes, and when it comes time to decide who does the really dirty work, they play rock-paper-scissors for it! Dean almost always loses, too, because he always throws the same thing...

Question 33

How does Dean refer to killing demons?

There are times that Dean hates his job - for obvious reasons. It's not easy dedicating a life to hunting demons, dying over and over, and losing the people you love... but there are other times that Dean most defintely finds the fun in hunting - and seems to really love what he and his brother Sam get to do. It's these times that he talks about killing monsters with absolute relish - and uses a very specific word when talking about it, too.

Question 34

What does Dean call the Impala?

There is no doubt that the Impala is one of Dean's most prized possessions - if not the most important thing he owns! He has loved this car since he was a kid, and takes incredible care of it - he's even re-built it when it was destroyed, and when they had to stop driving it for a while to stay under the radar, he hated having to get behind the wheel of anything else. What term of endearment does he use when referring to the car?

Question 35

Which of these realms has Dean been to?

Recent seasons of Supernatural have opened up the universe still futher, with alternate realities coming into play... but even other universes and parallel worlds aren't going to phase Dean Winchester - a man who has been to more 'realms' than anyone else on Earth. He's been to Heaven, Hell and Purgatory, and that's just the start! Undoubteldy, there are going to be more to come, as well... but of these four legendary realms, which has Dean been to on the show?

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