There's just something so incredibly innocent about Castiel when he first goes on a mission with Dean, especially when Dean has to turn Castiel's badge ride side up because Cas has it done all wrong.
Explaining the character of Castiel is a whole lot easier if you use Supernatural Season 8 Episode 8 as your guide. Castiel interrogates a cat, and it pretty much sums up his character up.
Dean just blurting out there is no singing in Supernatural easily sets the stage for the rest of the 200th episode that is so very special in its own right.
Sam losing his shoe on Supernatural Season 3 Episode 3 was the best. The poor guy was cursed by a rabbit's foot, and his luck just keeping get worse and worse.
Sam's aversion to clowns can always provide a few chuckles, but when he was getting chased on Supernatural Season 7 Episode 14, the absurdity of it all was good for some giggles!
Dean getting his Braveheart moment and using the speech from the movie was icing on the cake of a highly engaging episode. If anyone ever asks you why you can't stop watching Supernatural, just show them this one moment and walk away. Mic drop!
This is a controversial pick because many fans are over the Ghostfacer guys, but you had to laugh at these two morons when they first met Sam and Dean.
Dean's response to everyone's names never fails for a laugh. It was the moment that made it clear Supernatural doesn't take itself too seriously, and it's OK to laugh at some of the things they do.
Dean screaming at a Sam, who had no soul, to fight the fairies is one of the brightest moments ever to grace Supernatural. Dean didn't even care how crazy he appeared, he just wanted to get those darn fairies.
Dean screaming when the cat jumps out of the locker is a moment that will go down in Supernatural history. Of course, it turned out he had yellow fever, but seeing him get scared so easily was hilarious.
Why do they call this place The Empty? It's full. It's full of sorrow and despair playing over and over again of angels and demons dreaming about their regrets. Forever.