In the Supernatural season 12 episode “Regarding Dean,” Dean Winchester was cursed and slowly began to lose his memory, resulting in many silly moments. Whether he couldn’t remember the name for a lamp or his discovery that his job is fighting monsters, Jensen Ackles got to play up the comedic side that the show occasionally delivers.

Over more than 200 episodes, Supernatural has definitely given Dean a few other chances to be silly and funny. Whether he’s dying, fighting tiny beings with nipples or screaming at birds, here is my list of seven episodes to go back and binge-watch if you want to fully appreciate the sillier side of Dean Winchester.

Season 3, Episode 11: “Mystery Spot”

Usually dying is a very serious matter, but in this Groundhog Day-inspired episode, Dean got to die a bunch of times and Ackles made it funny and entertaining. The best part was a montage of Dean’s many deaths, including electrocution, slipping in the shower and a funny-tasting taco.

Season 4, Episode 6: “Yellow Fever”

Dean gets infected by a ghost that makes him afraid of everything, and the result is that Jensen Ackles gets to play the opposite of everything Dean really is. There are plenty of terrific and silly moments in this episode (his speech about hunting monsters or the ending sing-a-long to “Eye of the Tiger”), but the silliest comes when Sam opens a locker in an abandoned building. The only thing inside is a cute little kitty cat, but Dean is terrified, letting out a shrill, girlish scream accompanied by a perfectly delivered “That was scary!”

Season 5, Episode 8: “Changing Channels”

Dean got to be sillier and broader than ever before when the Trickster put the brothers in various TV shows, including a traditional sitcom complete with Dean’s very own catchphrase.

Season 6, Episode 9: “Clap Your Hands If You Believe…”

The silliest fight Dean has ever been a part of is definitely when he battled a fairy, a shining speck of light with nipples. Doing battle with such a tiny adversary offered plenty of opportunities for comedy, such as when he got arrested and demanded that Sam “Fight the fairies!”

Season 6, Episode 15: “The French Mistake”

This supremely meta episode saw Dean and Sam travel to a parallel universe where they were Jensen Ackles and Jared Padalecki, actors on a TV show called Supernatural. Watching Dean mock Jensen, particularly his time as a soap opera star, was a hoot.

Season 7, Episode 9: “How to Win Friends and Influence Monsters”

Dean’s love of fast food had dangerous consequences in this episode where the Leviathans drugged people via the Pepperjack Turducken Slammer. The result was ridiculous and kind of gross and Dean mindlessly stuffed his face and seemed clueless about everything.

Season 9, Episode 5: “Dog Dean Afternoon”

Here’s an easy recipe for silliness: Dean takes a potion to read a dog’s thoughts and then he begins to act like a dog. From yelling at birds to admiring the hindquarters of a suggestive poodle, it’s always funny when Dean acts in a very un-Dean kind of way.

Supernatural airs Thursdays at 8/7c on the CW.

(Image and videos courtesy of the CW and TNT)

John Kubicek

Senior Writer, BuddyTV

John watches nearly every show on TV, but he specializes in sci-fi/fantasy like The Vampire DiariesSupernatural and True Blood. However, he can also be found writing about everything from Survivor and Glee to One Tree Hill and Smallville.