Dean Winchester forms one-half of the awesome demon-hunting duo in Supernatural, as the brothers sacrifice everything to save the Earth from a bombardment of fantastical entities. Although Dean can exude quite a tough-guy, bad-boy attitude, he does not disappoint on the comedy front, as Jensen Ackles finds a direct connection to viewers' funny bones.
Most Supernatural fans are known to watch their favorite series on repeat; replaying their most cherished moments. Discover which fan-favorite episodes feature Dean's hilarious antics, as he portrays a variety of different personalities in the most humorous ways possible as Sam watches on, often in bewilderment.
10 Pudding! (Season 5 Episode 11)
Whilst undercover in a mental hospital, Sam and Dean find themselves in a sticky situation. On the verge of being busted with a dead man's brains in hand, Dean makes an impulsive decision of distracting the oncoming nurse and gives the perfect rendition of an unstable patient.
While many fans wish to be a fly on the wall, Dean drops his trousers and begins to vigorously jiggle his hips, providing some entertaining sound effects in the process. With a grand declaration of 'Pudding!", Dean thrusts his hands in the air like an excited kid, and the boys are escorted out by the bemused woman.
9 It's A Dog's Life (Season 9 Episode 5)
When the only witness to a horrific murder walks on four legs and barks, Sam finds an interesting way to break down the communication barrier. Thanks to a spell recorded by the Men of Letters, Sam provides his brother with the ability to speak to dogs (and other species too).
Dean quickly learns to enjoy the finer things in life as he begins to take on several canine-inspired traits. He causes a scene by getting into a heated argument with a pigeon, going so far as to draw his weapon on the vexing fowl. The cherry on top is when Dean lusts after a sultry-looking French Poodle, dishing out his iconic smoldering come-hither vibes for the pooch.
8 Cowboy Fanboy (Season 13 Episode 6)
The Winchester brothers show off their hats and spurs as the story takes a Western direction. Dean is over the moon about the opportunity to portray a cowboy, and completely geeks out when they arrive at the classic wild west themed hotel in Dodge.
Probably the happiest fans have ever seen Dean is when he enters the Wild Bill Suite, where he eagerly identifies all the legendary cowboys from their black-and-white photos and is practically giddy at discovering stirrup hangers.
Fun Fact: Sam uses the pseudonym Walker Texas Ranger in this episode; an accurate premonition of Jared Padelecki's future role in television.
7 LARPing (Season 8 Episode 11)
When the sister-he-never-wanted gets herself into trouble in Moondoor, the boys discover another level of undercover when they go LARPing to save the Queen. After their fake FBI guises are exposed, Dean is forced to immerse himself into the fantasy role play, claiming the role of Charlie Bradbury's servant.
Dean is all too willing to LARP, constantly distracted by Moondoor politics and forgetting that this is, essentially, a hunting case. In a dramatic ending, Dean gives a Braveheart-inspired speech, delivered with all the enthusiasm (and body paint) from the original film.
6 Dean The Virgin (Season 6 Episode 12 & Season 9 Episode 8)
When dragons seemingly develop a taste for virgins, the boys attempt to immerse themselves in a celibate community. While Sam has an easier time at it (a rather strange flex!), Dean is way out of his element and struggles to curb his sexual appetite, particularly after discovering a suspect who is anything but virginal. Viewers get a rare glimpse of Dean being awkward, as his embarrassment at discovering her history in adult films cannot be hidden.
Dean gets the opportunity to have his Excalibur experience and does not doubt his abilities in the slightest, until, however, he is amusingly bested by a rock. In an attempt to gain the upper hand, Dean invests in some explosives, and ends up destroying the sword in the process, well done!
5 Fight The Fairies! (Season 6 Episode 9)
When strange phenomena are reported from Elwood, the boys initially believe they are on a Mulder-and-Skully-type mission. While poking around a crop circle, Dean is accosted by a bright light and assumed to be in the middle of an alien abduction. In a hilarious recap of the attempted probing and slow dancing, Dean fills the Soulless Sam in on the details of his kidnapping, before stepping off to wash his 'violated' body.
If things aren't going badly enough, Dean is caught off guard and beat down... by a fairy! After introducing the tiny assailant to a microwave, Dean desperately tried to warn his brother, but unfortunately, the police intervene. Before being carted off, Dean yells "Fight the Fairies!" several times in a crazed attempt to inform Sam of the enemy.
4 Dean And The Bunny (Season 12 Episode 11)
Ever capable of making light of a serious situation, Dean befriends a cute little bunny after waking up in the middle of a forest. The party animal simply cannot remember the night before, but surprisingly alcohol isn't to blame, as the Winchester has been hexed by an unknown witch. Groggy and disorientated, he immediately cuddles the friendly rabbit and greets his new "buddy."
A memory-deficient Dean gives the impression of an excited schoolboy as he acts more like an ignorant GhostFacer than an experienced hunter. While slowly rediscovering the supernatural world, he has fans in stitches when he forgets how to drive Baby; is mind-blown by having an Angelic best mate, and freaks out over seeing a dead body.
3 Demonic Besties (Season 10 Episode 2)
The cutest thing to result from the Winchester's demonic adventures is when the Hunter and the King of Hell become besties. As Crowly and Demon Dean assess the Mark of Cain situation, Dean orders his buddy an elegant drink, a tiny umbrella included.
What may have looked like a mocking gesture, however, was in fact rather considerate. Knowing full well how much Crowly enjoys his cocktails, he saves him the embarrassment of ordering one for himself, how sweet! Some Princess Bride references are thrown in later for extra giggles before the truth of their bromance is revealed with an adorable photographic keepsake of the pair in matching outfits!
2 ScoobyNatural (Season 13 Episode 16)
In one of the most memorable cross-overs of all time, the Winchesters get animated as they join Scooby and the gang on some mystery-solving adventures. Being a cartoon clearly doesn't affect Dean's sex drive, as he does his best to achieve his childhood dream of hooking up with Daphne Blake.
Dean cannot contain his excitement for the situation as he valiantly defends his heroes from the dispirited Sam and Cas, joins Scooby and Shaggy during their iconic super sandwich munching snack breaks, and introduces the quirky characters to cussing.
1 Scaredy Cat (Season 4 Episode 6)
Fans get to see a different side of Dean when the usually hardcore hunter becomes a terrified wreck overnight. In arguably one of the most entertaining episodes of the franchise, "Yellow Fever" supplies a seemingly endless source of amusement, at poor Dean's expense.
Some of the top scenes include the time when Dean is too intimidated to handle a gun and volunteers to be responsible for the flashlight instead. His trusty 'weapon' is of no use, however, when Dean is terror-stricken after discovering a kitten, nor does it save him from being harassed by the spine-chilling pink-bowed Yorkshire Terrier.
Bonus: Eye Of The Tiger
Arguably the best Dean moment to ever be caught on camera is an unofficial content of Jensen Ackles goofing around on set during the Yellow Fever episode. Grateful fans were surprised by his performance after the end credits of the episode, whereby Dean reenacts his version of "Eye of the Tiger", air-guitar edition.
With Baby providing constant support and the perfect backdrop, Dean lipsynchs to every word as he busts a move or two, in a hilarious rendition of a classic rock song that will forever remain at the top of the list for Supernatural fans.