Supernatural: 10 Hilarious Winchester Brothers Memes That Will Make You Cry-Laugh

Fifteen years ago, the Winchester brothers burst onto television screens when Supernatural premiered in September of 2005. As the intense fandom that has grown around the show waits for its fifteenth and final season to resume in just a few days, on October 8, it is making everyone nostalgic.

Here we are taking a look at some of the funniest Winchester Brother memes that have been made over the years, so we can claim that the tears are from humor and not dismay at the final episodes starting to air. If Sam and Dean have done one thing better than save the world over the years, it has been to grace their audiences with humor so intense, it sometimes hurts.

10 Dean’s Internal Excitement vs. Sam’s External Excitement

This meme is the Supernatural fandom in a nutshell. The characters are reflected in their fans, and there are the Deans and the Sams. Deans always try to play it cool, though deep down, they are fangirling harder than anyone else. The Sams, they don’t play coy games. You know their feelings because they wear them on their sleeves.

Both kinds, however, won’t even care if you are a Dean, Sam, or Cas girl, as long as you are one of them. They will be excited to welcome you as a kindred spirit, get to know as much as they can about you in five minutes as they can (in their own, distinct style), and they WILL follow you on Tumblr.

9 Someone Ate Dean’s Pie

If there is one thing, every fan of the show knows, it is that as hardened and cold as Dean tries to appear, deep down, he is a big teddy bear. However, he has a few weaknesses that often show. Really, he only has two that can stop him: Sam and pie.

Dean Winchester will do anything for pie, and if you try to take it from him, this look will be just the beginning of the warning. Please do not touch it, and everything will be fine. Defy him, and prepare for no mercy.

8 Sam Has Mjölnir

This moment was one of the best in the series. When Sam has to strike down the deity Beau, who has joined Crowley in a fight against the brothers, it seems that this may be one battle two big for the demon-fighting duo. Luckily, caught in the middle of the battle is a gentleman who bought Mjölnir at an auction.

Apparently, Sam Winchester is worthy because he can wield the Thunder God’s hammer and strike down the deity. This meme is everything any fan from either fandom could want regarding this incident, especially Cas’s smile in reaction.

7 The Winchesters Are Scared Chuck Is Behind 2020

This meme is as terrifying as it is funny. In the grand scheme of life, knowing that Chuck is God and has put the brother’s through everything he has for his own amusement, this meme makes every true Supernatural fan bust out in laughter until that laughter is replaced with cold dread.

It is a little spot on for what would be happening if we lived in a world of the Winchester’s. This year definitely has the thumbprints of a bored greater being looking for sadistic humor all over it.

6 Winchester Brother Support – Really Non-Supportive

This meme is so funny because it tells the newly initiated fans everything they will ever need to know about the Winchester brothers being each other’s support system. The two love each other deeply. They are, however, not blind to the faults in the other ones. Sam knows that if Dean is admitting that he messed up, it could be anything from eating bad food to selling his soul to the devil – literally.

In their lifestyle, they do not have time to coddle and milk the other’s information. They have to be blunt and a little brutal, as Sam is here… but that only makes it funnier.

5 Even Sam Wonders How Dean Isn’t In Jail

This is one of the most asked questions amongst the faithful. From season one episode one, Dean shows he will do whatever it takes to survive and continue hunting. He has no problem committing fraud, swindling, cheating, and conning for money. He also has some severe anger issues that are not necessarily focused only on his supernatural foes.

Sam even wonders in the series how he evades capture. Though this is never his actual reaction, every fan knows that whenever he gets away with something really illegal, this is internal Dean.

4 Chuck Is Amused At The Brothers’ Horror

If the Winchester brothers had time to play Cards Against Humanity, Chuck would completely be eating popcorn while he messed with their minds. This meme is spot on for how a game for the brothers would likely go while God entertained himself, putting these types of responses in the deck.

It may be even funnier than this pairing could come up in an actual round of the game. It is likely if you are playing with Supernatural fans, their reactions would be similar to one of these three.

3 The Winchesters Insulting Each Other’s Looks Like Bosses

It is hard not to laugh at a meme that perfectly points out how Dean and Sam handle snipping at each other over their looks. It is a very brotherly thing to do, and this pair are brothers first and foremost. There is never going to be a time when Sam will not try and humble his older brother, nor will Dean ever let Sammie get away with thinking he has something up on Dean.

Though the rivalry between the two expresses itself in more violent ways, it is nice to settle on just trading barbs about fashion choices and not try to kill each other.

2 Dean Super Amused That Sam Is  STILL Afraid Of Clowns

Sam, being terrified of clowns, is one of the biggest punchlines in the world of Supernatural, and this is pretty spot-on for what Dean’s reaction is to it. Though there is proof in an early episode that Sam is very right to be afraid of clowns, Dean is not going to let it go that easily that the man who will give up himself to save the world can be sent quivering in terror at the sight of a white face with a red smile painted on it.

Dean laughing this genuinely is enough to make most fans join in, as it is not a common occurrence and one that they will gladly engage in.

1 Sam REALLY Wants Dean To Move On To The Point

There are a few simple rules in the show that are set early on in the series. Salt can hurt ghosts; religious symbols can save you from demonic possession and not mess with the Impala. Dean is attached to his car in the way a child grows attached to their lovey, but with much more aggression.

This moment is so perfect because Sam is trying to get on Dean’s level to show him the passion he feels on stopping this from happening, but in choosing this as his example, he loses Dean on a spiral of what would happen if someone ever took his baby.

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