Back in the ‘90s and early 2000s, writing and reading fan fiction was all the rage. I remember spending many hours reading fan fiction on sites such Fanfiction.net and FictionAlley.org. I even tried my hand at writing my own (terrible) fan fiction for Harry Potter, Lord of the Rings and later, Supernatural, but I never had the disciple required to finish my stories.
Even today, writing and reading fan fiction is still popular amongst fans of television shows such as Supernatural, although most writers have moved from FanFiction.net to sites such as Archive Of Our Own and even Tumblr.
If you’re having a bad day, suffering from the winter blues and can’t wait to see what is in store for Team Free Will, the following list of hilarious Supernatural fan fiction will definitely tickle your funny bone and make you giggle madly.
15 Cas Playing Matchmaker Is Always Going To End In Disaster
Griftings' hilarious fic takes place in an alternate universe where Castiel is forced to play matchmaker for Dean Winchester and Jo Harvelle so that their children will be the hosts for the archangel Michael and Lucifer. Of course, he fails miserably at his task and turns the whole affair into a hilarious romantic comedy in which Castiel and Dean fall madly in love. Needless to say, the Heavenly Host has mixed reactions to this entire affair while Lucifer, being Lucifer, attempts to troll his little brother by tricking him into inappropriately touching Dean’s backside during Castiel’s confessions of love. Broadway Musical is completely out there, but I could totally picture the rest of the angels (and Lucifer) making hilarious comments about Castiel’s relationship with Dean as only obnoxious older siblings can do to their long-suffering younger brother.
14 Dean + American Idol = LULZ
Rae666's drabble is a hilarious exploration about what poor Dean would say if he found out that his little brother Sam sneakily signed him up for the reality television show American Idol. Of course, the reality show ended in April 2016, but it’s still hilarious to imagine Dean’s reaction to being a contestant on American Idol even though the fan fiction is set when the Winchesters were still wanted by the FBI. I imagine that the long-suffering eldest Winchester would probably make sure that Sam wasn’t possessed by a demon who tried to trick the brothers and when he realized that his little brother was serious, he probably would pitch a fit. “I can’t sing, Sam! Why on Earth did you sign me up for the stupid television show?”
13 Sam And Dean Meet Robert Pattinson
Like most fans of vampire fiction, I absolutely loathed Twilight because it was just so dumb. Sparkly vampires, really? I’m all for reformed vampires, such as Henry Fitzroy in Blood Ties or even the Salvatore brothers from The Vampire Diaries, but Meyer’s depiction of the blood-sucking undead was utterly ridiculous. That’s why I laughed hysterically at OMG-Oriath‘s fic where Dean and Sam Winchester are hunting a vampire nest only to have their a**** saved by a machete-wielding Robert Pattinson. In this fanfiction world, Pattinson LOATHED playing a sparkly vampire and decided to take his hatred of Twilight out on real vampires. Too bad the CW couldn’t convince Pattinson to have a cameo, because that would have made for a great Twilight spoof that would have made all of the Supernatural fans cackle with glee.
12 Who Knew Dean Loved 'Rocky Horror Picture Show'?
MashiarasDream's fic takes place in an alternate universe where the Winchester brothers are in college and Dean is forced to play the role of Brad in The Rocky Horror Picture Show by his BFF Charlie. Of course, since practically every Supernatural fan ships Destiel (Dean/Castiel), he meets his co-star Castiel and the two flirt shamelessly. Thankfully, college-student Castiel is not as oblivious as his television counterpart, and quickly put the moves on Dean. Not that I can blame him, of course—Dean/Jensen Ackles is incredibly handsome with those big green eyes and adorable freckles. I’d love to see an alternate universe episode based on this ‘fic, although that is mainly because I think it would be a riot watching Jensen and Misha play Brad and Frank-N-Furter on-stage while their characters flirt with each other backstage. Then again, if they did that, the Destiel shippers would probably swoon with joy and break Twitter, Tumblr AND Facebook.
11 The Mental Image Of Dean As A Chef Is Priceless
EmWebb17‘s idea of having a hysterical alternate universe where Dean Winchester is actually a great cook who is working at Ellen Harvelle’s Roadhouse after being discharged from the Marines and gets tricked into appearing on America’s Next Top Chef is absolutely brilliant. I never really thought about whether or not Dean could cook, but I suppose it makes sense that he would actually be a pretty decent chef if life had different plans for the Winchesters. After all, I’m sure Dean had to teach himself to cook when his father John was off hunting and he had to keep an eye on Sam. While I wouldn’t be shocked if his first attempts were burnt messes, I’m sure with time, patience, and practice, he eventually got better at it.
10 Laundry Is Evil
I love Angeltrap‘s fic because I can TOTALLY buy Dean not wanting to use the laundromat because nowadays, they are too high-tech and he’s still stuck in the late 20th-Century, so he doesn’t know how to use them. He totally WOULD be the type to shoot the washing machine and dryer because he got so frustrated that he didn’t know how to use it. Of course, after he shot the machines to smithereens, he would add salt to the wound by ripping them away from the wall and smashing them up. Poor Dean—technology changes pretty quickly, so I can understand his frustration. However, you would think that Sam would force him to obtain a smartphone and that Dean would just google how to use a modern washing machine and dryer.
9 Even Death Needs A Vacation
Even though Dean supposedly killed Death in Supernatural season 11, O'MalleyTheAlleyCat's take is far more humorous and I could totally see the writers pulling something like this in season 12. Instead of “dying,” Death merely decided it was time for him to take a vacation. His reasoning in the story was that Chuck/God had taken a vacation, so why not the eldest of the Four Horsemen of the Apocalypse? Of course, the icing on the cake is the mental image of Death chilling on a beach with cartoon skull surfer shorts and sunglasses with cute skull emojis on the sides. If the showrunners ever decide to bring the character back in a future season, I hope they go with the idea that he took a vacation because it would be a riot to see Julian Richings chilling out on a beach somewhere sipping daiquiris.
8 Chuck And Lucifer Watch Hilarious Home Movies
I was rolling at the idea that Amara facilitates a reconciliation between Chuck/God and his rebellious son, Lucifer in Monkeygirl77 's story. Plus, the mental image of Chuck watching home movies of a wee Lucifer running around is pretty cute too. But I cackled the most out of the scene when Chuck and Lucifer make amends with one another not by having a heart-to-heart chat, but by Chuck tickling his son until he starts laughing hysterically and forgives his father. I can totally picture Rob Benedict and Mark Pellegrino re-enacting this scene at a convention, and I’m pretty sure everyone would laugh hysterically. Too bad this isn’t how the Supernatural writers chose to reconcile Chuck and Lucifer on the show. It would’ve been a riot to see God himself and the literal Devil having a tickle fight and watching embarrassing home videos.
7 Team Free Will Texts When They Are Bored
Okay, some there are definitely a few grammatical errors in CastielWinchester101‘s fic that make my inner editor facepalm, but it does add a touch of authenticity to the story. After all, it’s not like we all have perfect grammar when we’re texting our friends. I know if I am in a hurry or distracted, my texts and Facebook messages are filled with all sorts of hilarious typos. Aside from the amusing grammatical errors, the part where Dean attempts to tell Cas a “knock, knock” joke via text message is a hoot because the angel is SO confused. Honestly, I’m shocked that didn’t happen in the show. I can imagine Dean and Sam purchasing a cell phone for Cas to use, and the angel asking them “What the hell is this contraption, and how do I use it?”
6 Dean Is A Sucker For Cute Fluffy Puppies
I won’t lie, I squealed at the mental image of Dean, Sam, Castiel, Charlie and Kevin adopting a stray Golden Retriever puppy that they found in the woods. SuicidalUnicorn79 is a genius for including a sweet scene where Cas is holding the puppy like a baby. Honestly, if the Supernatural showrunners wanted to make every animal lover melt, they’d include a scene in an episode where Team Free Will is playing with adorable puppies. It would be SO cute watching Dean, Sam and Cas snuggling with a tiny puppy. I also laughed that the author chose a Golden Retriever mix as the breed that won Dean over because I know that Jensen Ackles owns an adorable Goldendoodle named Oscar as well as a very sweet Cockapoo named Icarus in real life.
5 Even Lucifer Enjoys Trolling The Winchester Brothers
I’m rolling at MistressPandora's idea of Lucifer (in Castiel’s body) starting a prank war on the Winchester brothers because OF COURSE he would. I’m sure when Lucifer, Michael, Adam and Sam were locked in the cage, the Lucifer and Michael started trolling Sam out of sheer boredom because he’s so easy to annoy and they needed a good laugh. Plus, Lucifer IS Gabriel’s older brother, and I’m sure the two were quite the mischief-makers when they were young. The scene where Chuck teleports his unruly son and the two Winchester brothers is also funny because I can totally buy Lucifer trying to pull a prank on his dad. Of course, Chuck has HAD it with his rebellious son and his stupid prank war, which further adds to the hilarity.
4 Dean And Sam Should Team Up With Darcy Lewis
AForgottenWeasley's s idea of having the Winchester brothers meet Darcy Lewis, who is now an agent of SHIELD, is absolutely brilliant because it makes perfect sense that if they existed in the same universe, their paths would cross. Darcy would definitely take the whole supernatural thing in stride. I mean, after helping Thor and Jane to defeat Malekith in Thor 2: The Dark World, I doubt that learning that creatures such as werewolves and vampires are real would phase her. Although I’m curious as to how a Marvel/Supernatural crossover would work, given that the now deceased archangel Gabriel pretended to be the Norse god Loki, and there’s already a Loki in the comics. Perhaps, since both Lokis are known to be shape-shifters, Gabriel took the form of Tom Hiddleston’s Loki on Earth and just pretended to be the real Loki.
3 Dean Really, Really Hates Flying
Moonshayde‘s fan fiction about a missing scene from the season six episode Weekend At Bobby’s is adorable because poor Dean still hasn’t gotten over his fear of flying. It’s a shame that the writers didn’t include a funny scene like this in the episode where the poor guy had to figure out a way to manage his phobia….or, well, attempt to manage his phobia while traveling to Scotland in order to locate Crowley’s bones. I can totally imagine Dean trying to calm down by listening to Metallica, only to feel queasy once the plane took off. Honestly, Sam should pack something like Dramamine when they two are forced to fly. That way, Dean will be drowsy enough that he’ll be able to fall asleep on the flight and won’t get sick.
2 Sam Winchester Has Bad Taste In Women
DarkBeauty216 is a genius because I can totally believe that Dean would have a crush on Lucy Lawless as Xena, Warrior Princess while Sam would have no idea why his brother was so in love with a fictional Amazon warrior. Needless to say, poor Sam learned the hard way in this story about why you don’t want to mess with a die-hard Xena fanboy, as Dean tackled him and initiated a full-blown wrestling match. To add insult to injury, Dean would only let Sam go if he promised to serve his older brother breakfast in bed. Sure, Sam’s the taller of the two brothers, but hell has no fury like a Xena/Lucy Lawless fanboy who has been scorned and who has felt the need to defend his crush’s honor against people who don’t have any appreciation for classic pop culture.
1 Dean Just Wants To Use The Grenade Launcher
I can’t stop laughing at DeanAndSam's fan fiction, which takes place after season 12, episode five because in the story, Dean is obsessed with the grenade launcher and was VERY sad that he didn’t have the opportunity to use it in The One You’ve Been Waiting For. Of course, Dean stubbornly insisted on using the grenade launcher despite Sam’s better judgment. Even though it is hilarious to imagine the elder Winchester’s glee at FINALLY having the opportunity to use such a cool weapon, Sam does have a good point—they are hunters, and their best weapon is stealth. Using a grenade launcher is way too conspicuous, and it is not like they could use it against the usual assortment of spirits, demons, and other paranormal creatures they encounter.