Top 5 Funniest Dean Winchester Moments

Hunter. Hero. Hilarious.

He’s been slaying monsters and saving innocents for thirteen seasons, yet the eldest Winchester only seems to be getting funnier. While he’s got enough quips, jokes and smouldering good looks to fill up an entire encyclopedia, these five particular moments will undoubtedly go down as Dean’s greatest hits!

Fair warning, there are SPOILERS AHEAD!

#5: Dean Winchester Is…Batman
“Bad Day at Black Rock”

The two brothers end up encountering a rabbit’s foot; a cursed object that brings both good and bad luck to its users. After losing it, Sam’s bad luck ultimately leads to him being captured by two madmen who have been hunting him. Dean manages to recover the rabbit’s foot, using the tremendous luck to rescue Sam in a ridiculous series of coincidences. He easily dodges blows and even tosses a pen into a gun barrel. Dean’s revelry in his luck is just icing on the cake. “I’m Batman!”

#4: Busty Asian Beauties
“Tall Tales”

While investigating 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 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 by far its most memorable.

#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. Woof, woof!

#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. 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”

In order to find the source of a string of supernatural killings, the Winchesters get themselves committed to a mental institution . The fact that they fit right in with the mentally ill by telling the staff the truth about what they do makes for some unabashedly funny moments, the most iconic of these being 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. Our hero everyone.

Be sure to check out the video below to see our picks for the Top 10 Most WTF Supernatural Episodes!