Top 10 Funniest Castiel Moments on Supernatural

Deciding he wants to be a hunter of the supernatural, like his friends the Winchester brothers, Castiel helps them find an unusual case. While questioning a confused elderly woman at a care facility, she tells the trio that their cat talks sometimes and it seems to hate a mouse. Cas takes this completely seriously, volunteering to interrogate the feline. When Dean and Sam are ready to leave, Castiel claims to have nearly gotten the cat to tell him what it knows, but the boys insist on leaving. The real capper is the cat really speaking as he leaves. “Dumbass.”

On a similar subject, with Dean and Sam taking some time apart from one another, Castiel enlists Dean’s help in finding the archangel, Raphael. After discovering the aftermath of the angel’s battle with demons, the two of them pose as FBI agents, as the Winchesters are prone to do. However, Cas is significantly less experienced with acting, and lying in general, than they are. From holding his badge upside down, to telling the officer they interview the truth about what happened, Castiel’s inability to play the part is rather adorable.

After an angel assassin is sent back in time to kill their parents, Sam and Dean turn to Castiel for a similar trip back to the past to stop it from happening. However, Castiel reveals that since he’s on the outs with Heaven, that sending them to the past will be difficult for him. Dean likens him to a DeLorean without enough plutonium, ala “Back to the Future.” But Castiel flat out tells him: “I don’t understand that reference.” Castiel’s cluelessness about pop culture is one of his more endearing and funny qualities, and this moment helps sum it up perfectly.

Season 7 sees Cas somewhat worse for wear, as, after going full villain, he returns… out of sorts. More on that later. For now, let’s focus on his reunion with Crowley, the demon whom he once partnered with. When the new King of Hell arrives at Bobby’s place to spar with the Winchesters, and maybe help them, the demon tries to do the same with Castiel, only to be taken aback when Cas starts rambling randomly about insects and honey; leaving the witty villain nearly speechless. The only thing that might have put him off more would be if Cas offered to play Twister with him.

While hunting for the mother of monsters, Eve, the Winchesters, Bobby, and Castiel track their quarry to Oregon. Stopping at a diner, Castiel offers to search the town for her using his angel powers, which let him move quickly through teleportation. However, instead of vanishing, he remains seated in the booth. Dean is incredulous that Cas has been rendered impotent by Eve, “Figuratively,” and tells him that without his powers he’s just a “baby in a trench coat.” Instead of replying, Cas turns and looks out the window in silence; pouting in a very funny way. “I think you hurt his feelings.”

We’ve talked about Castiel’s loopy period before, but its beginnings offer some of the funnier material. Having taken on Sam’s memories of Hell, Cas is now in a mental hospital, due to how much his mind has been damaged from the experience. His conversation with Sam and Dean when they meet him again veers wildly between topics, though animals are a common theme, and his delivery is absolutely hilarious. Loopy Cas leaves quite a funny impression, though not quite as impactful as the one he leaves on poor Kevin Tran: “Boop.”

Continuing the theme of Castiel acting out of his usual character, Dean finds an unusual version of his angelic friend after another winged messenger sends him into a possible version of the future. In this post-apocalyptic world, Dean meets a de-powered, human Castiel, who has become something of a hippie; engaging in hedonistic activities like orgies and drugs. Seeing the usually high strung or overly serious Cas relaxed and playing the love guru is an absolute blast. It’s a shame it took the end of the world for us to see it, though.

After Castiel’s faith in God has been shaken in the previous episode, Sam calls on Castiel for help. Literally. On his phone. Love his voicemail message, by the way. However, the angel has taken his lost faith harder than even most humans. Although plenty of people turn to alcoholism after a crisis, few of them can handle the volume that Cas does. “’I found a liquor store.’ ‘And?’ ‘And I drank it!’” As it turns out, despite how nice he usually is, Cas is actually kind of a mean drunk and his drunken and hungover outbursts are pretty dang amusing.

For being a millennia-old being of celestial intent, Castiel can be surprisingly innocent about a lot of things. Such is the case when he discovers porn. While watching it in the same room as Sam and Dean (which is a definite faux pas), Cas is puzzled by the “plot,” wondering why the pizza delivery man would spank the cheerleader if he loves her. This is made even funnier when the demon Meg kisses him later in the episode to take his angel blade and Cas responds enthusiastically; citing “the Pizza man” as the one he learned it from. Classic!

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

“I Was Never in Your…”
“Mommy Dearest”

People Skills
“The Third Man”

Protection
“I’m No Angel”

Cas Decides to Become a Hunter
“Hunteri Heroici”

What God Looks Like
“Peace of Mind”

The climactic showdown of Season 5 sees Michael and Lucifer confront one another, with their prophesied battle said to bring about the Apocalypse. However, Team Free Will is there to rain on their parade, with Dean stepping in to let Sam, whom Lucifer is possessing, that he won’t abandon him. In order to give them time to talk, though, Castiel and Bobby arrive, with Cas lobbing a holy oil Molotov cocktail at Michael to temporarily banish him, but not before uttering one of the funniest exclamations in the show’s long history: “Hey, assbutt!” Cas tries and fails so hard to sound cool that it loops back around into amazing territory.