Top 20 Funniest Dean Winchester Moments on Supernatural

what's the matter cat got your tongue tough crowd welcome to Miz Mojo and today we're counting down our picks for the most hilarious moments from Dean Winchester on Supernatural that was scary number 20 trying to act perhaps one of the funniest Supernatural episodes ever see Sam and Dean transported to the real world their reactions to their actors lives and Supernatural the TV series are absolutely priceless come on look at these maale modeling sons of nice blue steel Sam hey apparently it's our job 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 we need to get all three of that crap what so he does it oh here do we really need all these lies of me I I I you know I think we've covered it though honestly if someone told us to act like ourselves we're not sure we'd do any better number 19 shot the sheriff one of the Winchester's most Ardent human antagonists is FBI agent Victor henriksson henriksson 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 I got a lot to celebrate I mean after all seeing you two in chains you kinky son of a we don't swing that way that's funny the demon-possessed henriksson is insistent on keeping the Winchesters in the jail even going so far as to kill the sheriff thankfully Sam and Dean exercised the offending demon saving henriksson 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 I Shot the Sheriff but you didn't shoot the deputy though knowing him he's probably more familiar with the Eric Clapton version I owe you the biggest I told you soever number 18 Harry Palms the Winchesters encounter all manner of strange phenomena in their travels but when they come to one town they investigate superstitions or make belief stories that have come to life examples include an attack by a tooth fairy someone's face getting stuck that way and other nonsense I didn't know it would really work what would work all I did was shake his head 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 effects radius and apparently an old wife's tale about getting hairy Palms from too much self-love has apparently come true I got bored the nurse was hot you know you can go blind from that too give me 5 minutes we'll go check out that house luckily the boys managed to get to the bottom of things before any of the other myths about that activity become real number 17 nunar 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 we're out there was a half a bag yesterday I killed it 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 seriously dude it's like noon uh well you drank all the coffee so what am I supposed to drink water Dean really should drink more water staying hydrated is important for everyone particularly for someone who saves the world is frequently as he does number 16 posy magnet the boys travel back in time sever 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 we're to form a posy then we the string Finch up right put a bullet in his head for good measure that actually sounds like a good plan a posi is being put together to take down the Phoenix Elias Dean suggests that Sam ride out to find Colt while he joins the posy he also has a little too much fun with the word posy and it's similarity to a word we probably can't say hook up with a posi cuz you know me I'm a posi magnet I mean I love posy make that into a t-shirt number 15 hunky dory spells and other strange effects hit the Winchesters just as often as monsters do in one case Dean comes down with a bad cave Cas 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 this is a coat this is a a light stick however one thing he doesn't forget is Finding Nemo and the movie's character Dory who has similar memory issues if a witch got a clear shot of me I would be dead okay I wouldn't be freaking uh Dory Dory not going to apologize for loving that fish not to you not to anyone while the Pixar movie doesn't seem like Dean style this just proves that the Studio's animated films can affect even the most hardened hearts or seemingly absent Minds number 14 meeting Professor Redfield 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 guys as FBI agents the Winchesters interview the man Professor Redfield call me Donatello I'm named after him the Mutant Ninja Turtle the Renaissance sculptor 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 met a Leonardo or Michelangelo then they'd have the full set ra nice meat suit number 13 mugshot the Winchesters go to Great Lengths to resolve some of their cases I hate this plan then yeah I got that the first 10 times I heard it 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 get getting his mug shot as seriously as he takes everything else that is not very I call this one the blue steel yeah that's right who do you think wore better Zoolander or Winchester number 12 fight the fairies 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 close encounter close encounter close encounter what kind first second they're after me 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 plus Community fight the fairies you fight those fairies fight the berries number 11 Dean's ruena impression 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 turned to Rowena their powerful witch Frenemy Rowena tells the boys they need to collect enough souls for her to build a bomb okay so if we got this kind of juice then what you get me enough Souls I can 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 it's a book of the Damned spell boyos take this we Crystal it'll suck up all the blimy ghosts just say the magic word we didn't Ain how Sam isn't rolling with laughter at his impression because we certainly are but then we never stood a ghost of a chance number 10 demon karaoke I my love 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 and up with Crowley one of demon Dean's favorite activities is getting drunk and singing songs like I'm Too Sexy and Imaginary Lover Imaginary Lover never turn you down his drunken warbling clashes wonderfully with the image of villainy that demons project then again given his fellow Patron hatred of his singing Maybe demon is conducting a more subtle form of evil number nine Dean just can't stop dying I'm not going to die not today 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 demise has 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 who wants Chinese Sam's exasperation contrasted with Dean's obliviousness along with his enjoyment of the song that plays every time Sam starts again make first some hilariously dark comedy that can be enjoyed regardless of whether or not it's In the Heat of the Moment of [Music] the number eight mouthful of candy what do you mean 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 right and that's how it really happened the brothers narrate their exploits and try to make the other look bad leading to a number of funny moments throughout whoa whoa whoa who hold on a minute what 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 who was he with come on I ate one maybe two just let me tell it okay number seven cheeseburger extra onions I love a cheeseburger extra onions 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 seen in the past to fit in on the inside come on man you're like Clint Eastwood from Escape from alcatra 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 number six Dean the gym teacher a game with one simple rule Dodge in order to investigate a case of student possession at one of their old high schools Dean and Sam go undercover a St Sam as a janitor and Dean as a gym teacher Dean gets into character in the most hilarious of ways Dawning a stereotypical outfit complete with red shorts as well as berading his charges in a pseudo military fashion full of over-the-top machismo hang a Laugh funniest of all though is how much enjoyment Dean takes in the power he has over the kids the whistle makes me that God number five Dean Winchester is Batman that a rabbit split the two brothers in 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 whoa okay okay now hold on a minute 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 number four busty Asian beauties dude were you on my computer 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 uh busty Asian beauties.com Dean is speechless for once and his expression is absolutely Priceless although busty Asian beauties become something of a running gag on the show the sight's first appearance is its most memorable and provides one of Dean's most humorous moments de would you just don't touch my stuff anymore okay number three Man's Best Friend wait a minute can I hear all animals yep animals have a universal language 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 well I'm sure you'll be out of here soon please I'm 14 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 [Music] poodle [Music] number two scaredy-cat I'm not going in there 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 freakouts occur when the pair investigates an abandoned warehouse and happen upon a stray cat inside a locker eliciting a shrill scream from the terror prone [Applause] Dean before we continue be sure to subscribe to our Channel and ring the bell to get notified about our latest videos you have the option to be notified for occasional videos or all of them if you're on your phone make sure you go into your settings and switch on notifications number one the perfect disguise 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 demon signs I hunt demons Monsters the most hysterical moment happens when the two look through the morg and are caught in the act Thinking Fast Dean drops his pants and pretends to be childishly enjoying his partial state of undress pudding 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 you know what you're awesome do you agree with our picks check out this other recent clip from M Mojo and be sure to subscribe and ring the bell to be notified about out our latest videos

Channel: MsMojo

Views: 122,691

Keywords: Comedy, Sitcom, Streaming, TV, dean winchester, dean winchester lines, dean winchester moments, dean winchester quotes, funniest, funniest dean winchester moments, funniest dean winchester moments on supernatural, list, mojo, msmojo, sam and dean, sam and dean moments, sam interrupted, sam winchester, supernatural, supernatural moments, top 10, watch mojo, watchmojo, winchester, winchester moments

Id: RQvHSVB3BVo

Length: 17min 11sec (1031 seconds)

Published: Tue Mar 12 2024