Top 20 Funniest Dean Winchester Moments on Supernatural
#20: Trying to Act
“The French Mistake”
Top 10 Funniest Dean Winchester Moments on Supernatural
Perhaps one of the funniest “Supernatural” episodes ever sees Sam and Dean transported to the “real” world. Their reactions to their actors’ lives and “Supernatural” the TV series are absolutely priceless. However, our favorite moment is when the boys try their hands at acting. The Winchesters have saved the world multiple times, but it turns out all their enemies had to do was stick them in front of a camera! Watching Dean (and Sam) fail their way through numerous takes has us laughing and cringing in equal measure! Though honestly, if someone told us to act like ourselves, we’re not sure we’d do any better.
#19: Shot the Sheriff
“Jus in Bello”
One of the Winchesters’ most ardent human antagonists is FBI agent Victor Henriksen. Henriksen is overjoyed when he finally captures the duo and holds them in jail. As funny as Dean’s remark on Henriksen’s tastes in the bedroom is, the agent’s eventual possession leads to an even more amusing joke. The demon-possessed Henriksen is insistent on keeping the Winchesters in the jail, even going so far as to kill the sheriff. Thankfully, Sam and Dean exorcize the offending demon, saving Henriksen. The FBI agent is understandably shaken up at what he’s done, so Dean attempts to comfort and lighten the mood by quoting a Bob Marley song - though, knowing him, he’s probably more familiar with the Eric Clapton version.
#18: Hairy Palms
“I Believe the Children Are Our Future”
The Winchesters encounter all manner of strange phenomena in their travels. But when they come to one town, they investigate superstitions or make-believe stories that have come to life. Examples include an attack by a tooth fairy, someone’s face getting stuck “that way,” and other nonsense. After Sam returns to their motel room, he details to Dean the locations of all the incidents. However, Dean has discovered the hard way that their room is within the effect’s radius. And apparently, an old wives’ tale about getting hairy palms from too much self-love has apparently come true. Luckily, the boys manage to get to the bottom of things before any of the other myths about that activity become real.
#17: Nooner
“The Vessel”
When the Winchesters aren’t out hunting monsters, chances are they’re researching ways to fight them better. Dean wakes up one morning to find that Sam has consumed their entire supply of coffee, while researching a weapon to fight Amara, their current big bad. With seemingly no better options, Dean turns to his other favorite drink - beer. Although Sam is incredulous, Dean refuses to go for the easy option. Dean really should drink more water. Staying hydrated is important for everyone, particularly for someone who saves the world as frequently as he does.
#16: Posse Magnet
“Frontierland”
The boys travel back in time several times during the series. Their trip to the old American West yields plenty of comedic opportunities. Unfortunately for them, their goal, the supernaturally powerful Colt pistol proves difficult to come by, as does its maker, Samuel Colt. Not only that, but there's a phoenix in town, and it's out for revenge. A posse is being put together to take down the phoenix, Elias. Dean suggests that Sam ride out to find Colt, while he joins the posse. He also has a little too much fun with the word posse and its similarity to a word we probably can’t say.
#15: Hunky Dory
“Regarding Dean”
Spells and other strange effects hit the Winchesters just as often as monsters do. In one case, Dean comes down with a bad case of memory loss. While it’s also played seriously, in many cases in this episode, it’s also a great source of laughs. From forgetting what a lamp is to his own name, Dean’s selective amnesia is pretty funny. However, one thing he doesn’t forget is “Finding Nemo,” and the movie’s character Dory, who has similar memory issues. While the Pixar movie doesn’t seem like Dean’s style, this just proves that the studio’s animated films can affect even the most hardened hearts - or seemingly absent minds.
#14: Meeting Professor Redfield
“All in the Family”
Sam and Dean’s encounters with the supernatural often leave them interviewing the survivors of disasters and attacks by creatures. When a deadly fog runs through an Oklahoma town, the only thing more unusual is that one man survives it. In their usual guise as FBI agents, the Winchesters interview the man, Professor Redfield. He prefers to be called by his first name, though Dean believes his namesake is a “hero in a half-shell” rather than the Italian visual artist. It’s just too bad he and Sam never meet a Leonardo or Michaelangelo - then they’d have the full set!
#13: Mugshot
“Folsom Prison Blues”
The Winchesters go to great lengths to resolve some of their cases. One of their most drastic early adventures sees them get arrested on purpose. How else are they supposed to take care of a ghost terrorizing inmates in a prison? While their arrest is complicated (more on that later), it does lead to some funny moments. One of these (again, more later) sees Dean take getting his mugshot as seriously as he takes everything else - that is, not very. Who do you think wore it better: Zoolander or Winchester?
#12: Fight the Fairies
“Clap Your Hands If You Believe”
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Dean’s close encounter with a UFO leads to plenty of hilarity. Especially since it turns out that he was abducted by fairies, not aliens. Still, for as absurd as his first reaction to seeing a fairy is, it’s even funnier to see everyone else’s reaction to his antics when he mistakes a little person for the offending sprite. We all know that Dean is at the very least an ally, but the people watching him attack a person of short stature and calling him a fairy get very much the wrong impression about Dean’s attitude towards the LGBTQIA+ community.
#11: Dean’s Rowena Impression
“Alpha and Omega”
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When stabbing the villain with something pointy isn’t enough, the Winchesters sometimes have to turn to magic. Such is the case with Amara, God’s sister. For help, Sam and Dean turn to Rowena, their powerful witch frenemy. Rowena tells the boys they need to collect enough souls for her to build a bomb. When they get to the haunted sanitarium where they’re supposed to get the job done, Dean is less than enthused by the prospect, sarcastically imitating Rowena’s Scottish accent. We “dinnae ken” how Sam isn’t rolling with laughter at his impression, because we certainly are! But then, we never stood a ghost of a chance!
#10: Demon Karaoke
“Black”
Following the season 9 cliffhanger that saw Dean become a demon, fans were left wondering what heinous crimes the newly demonic Winchester would commit once he reappeared. As it turns out, the first and greatest of these would be – karaoke. While living it up with Crowley, one of demon Dean’s favorite activities is getting drunk and singing songs like “I’m Too Sexy” and “Imaginary Love.” His drunken warbling clashes wonderfully with the image of villainy that demons project. Then again, given his fellow patrons’ hatred of his singing, maybe “Deanmon” is conducting a more subtle form of evil.
#9: Dean Just Can’t Stop Dying
“Mystery Spot”
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During the third season, Sam Winchester finds himself repeating the same day over and over again. The common factor in every new day he experiences is that Dean dies. While Dean’s deaths are occasionally somber, the manner of his demises become increasingly ridiculous, from being electrocuted, to slipping in the shower, to getting poisoned by a taco, and even getting squashed beneath a desk like a cartoon. Sam’s exasperation contrasted with Dean’s obliviousness, along with his enjoyment of the song that plays every time Sam starts again, make for some hilariously dark comedy that can be enjoyed regardless of whether or not it’s in the “heat of the moment.”
#8: Mouthful of Candy
“Tall Tales”
This moment occurs during an episode in which Dean and Sam recount to their friend Bobby their investigation of a case in which several urban legends, including alien abductions and alligators in the sewers, have seemingly come true. The brothers narrate their exploits and try to make the other look bad; leading to a number of funny moments throughout. However, the funniest of these is definitely when Sam claims that when the pair investigate a dead professor’s office, Dean stuffs his mouth nearly to bursting with candy that he finds. This causes his cheeks to bulge, making him look ridiculous, and leaving him barely able to speak.
#7: Cheeseburger, Extra Onions
“Folsom Prison Blues”
The Winchester brothers are no strangers to being on the wrong side of the law, so they don’t have to act much when they have to infiltrate a prison to investigate some supernatural killings. As previously mentioned, Dean in particular takes the whole thing rather lightly, drawing on prison movies he’s seen in the past to fit in on the inside. His crowning moment of irreverence, however, occurs during his initial interrogation by the FBI, which sees him place a food order. Upon being asked if he thinks he’s funny, Dean replies, [“I think I’m adorable.”] And we’re inclined to agree!
#6: Dean the Gym Teacher
“After School Special”
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In order to investigate a case of student possession at one of their old high schools, Dean and Sam go undercover as staff – Sam as a janitor, and Dean as a gym teacher. Dean gets into character in the most hilarious of ways, donning a stereotypical outfit (complete with red shorts), as well as berating his charges in a pseudo military fashion full of over the top machismo. Funniest of all though, is how much enjoyment Dean takes in the power he has over the kids. “The whistle makes me their god.”
#5: Dean Winchester Is… Batman
“Bad Day at Black Rock”
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The two brothers encounter a cursed object that brings both good and bad luck to its users – a rabbit’s foot. After losing it, Sam’s bad luck ultimately leads to him being captured by two men who are hunting him. Dean recovers the rabbit’s foot and uses the tremendous luck it grants him to rescue Sam in a ridiculous series of coincidences that make it seem like child’s play: easily dodging blows and even tossing a pen into a gun barrel! Dean’s reveling in his luck is just icing on the cake. “I’m Batman!”
#4: Busty Asian Beauties
“Tall Tales”
In another moment from the episode in which Sam and Dean investigate urban legends, Sam sits down to use his laptop, only to find it frozen. He asks Dean if he used his computer, and while Dean denies it, Sam then wonders why the screen is stuck on “BustyAsianBeauties.com.” Dean is speechless - for once - and his expression is absolutely priceless. Although “Busty Asian Beauties” becomes something of a running gag on the show, the site’s first appearance is its most memorable and provides one of Dean’s most humorous moments.
#3: Man’s Best Friend
“Dog Dean Afternoon”
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While on a case, the boys discover that the only witness they have is of the canine variety, leading Dean to take a potion that allows him to understand dogs. As it turns out, the spell lets him understand all animals, as well as take on the characteristics of a dog. The former leads to an amusing argument with a pigeon over the state of Dean’s car, while the latter causes him to engage in typical dog behavior, including sticking his head out of car windows, playing fetch, and even making eyes at a French poodle.
#2: Scaredy Cat
“Yellow Fever”
Upon being infected with a ghostly contagion, Dean becomes frightened very easily. Seeing the usually stoic and unflappable hero freak out at the drop of a hat predictably provides a lot of comedy. While some of his terrors are hallucinations, many of them result from his being scared of everyday things, or at least things the Winchesters deal with on a daily basis. The funniest of these freak-outs occurs when the pair investigates an abandoned warehouse and happen upon a stray cat inside a locker, eliciting a shrill scream from the terror-prone Dean.
#1: The Perfect Disguise
“Sam, Interrupted”
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Just like when they infiltrated the prison, the Winchesters get themselves committed to a mental health institution to find the source of a string of supernatural killings. The fact that they’re able to fit right in with their fellow patients by telling the staff the truth about what they do is very funny and leads to some insights into their characters as well. The most hysterical moment happens when the two look through the morgue and are caught in the act. Thinking fast, Dean drops his pants and pretends to be childishly enjoying his partial state of undress. Meanwhile, thanks to his completely unexpected and playful act, we can’t help but giggle childishly ourselves!
Is there a Dean moment you find awesomely hilarious that we forgot? Share your favorites in the comments!
