Top 10 Funniest Dean Winchester Moments on Supernatural
Top 10 Funniest Dean Winchester Moments on Supernatural

Top 10 Funniest Dean Winchester Moments on Supernatural

Script written by Garrett Alden

These are the funniest Dean Winchester Supernatural moments! For this list, we'll be looking at the moments of hilarity involving the elder Winchester brother, Dean. Because he presents himself as a serious, tough guy most of the time, Dean's goofier moments are all the funnier. Also, a few of these moments have some plot importance, so there will be some spoilers ahead! We've included moments like Dean karaoke, when Dean just can't stop dying, when Dean Winchester is batman, that time when he pulled his pants down and yelled pudding! and more!

Top 10 Funniest Dean Winchester Moments From “Supernatural”

This hunter is monstrously funny. Welcome to MsMojo and today we’ll be counting down our picks for the Top 10 funniest Dean Winchester Moments From “Supernatural.”

For this list, we’ll be looking at the most hilarious moments involving the eldest Winchester brother, Dean. Because he presents himself as a serious, tough guy most of the time, Dean’s goofier moments are all the funnier. Beware that there will be some spoilers ahead.

#10: Demon Karaoke


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”

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 he finds; causing 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. 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”

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”

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 where 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 “” 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 funniest moments.

#3: Man’s Best Friend

“Dog Dean Afternoon”

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.

Before we get to our top pick, here are a few honorable mentions:

His ‘Blue Steel’ Mugshot

“Folsom Prison Blues”

My Boobs


Posse Magnet


#1: The Perfect Disguise

“Sam, Interrupted”

Just like when they infiltrated the prison, the Winchesters get themselves committed to a mental institution to find the source of a string of supernatural killings. The fact that they fit right in with the mentally ill by telling the staff the truth about what they do is very funny and leads to some insights into their characters as well. The funniest 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 nudity, making for our favorite funny Dean moment.