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Supernatural's 10 Funniest Castiel Moments From All 15 Seasons


  • Castiel’s late addition to Supernatural led to his transformation from a celestial being to a funny and loyal ally to Sam and Dean.
  • Cas’s humorous missteps, like interrogating a cat and drinking a liquor store, showcase his innocence and adaptation to human life.
  • Despite Castiel’s angelic powers, he remains awkward and funny even in intense situations, proving to be one of the show’s most entertaining characters.

Supernatural’s Castiel is one of the most entertaining characters on TV, with a seemingly endless capacity for humor on display throughout the show’s run. Castiel is one of the most entertaining parts of the show, but he was a late addition to the cast. He first appears at the start of season 4, but at that point, he remains a powerful and mysterious celestial being who presents a threat to Sam and Dean.

Then in Supernatural season 5, Castiel begins to undergo a transformation as he experiences a faith crisis. Castiel changes from a mindless servant, to a thinking, emotional, and curious being. This leads to him joining Sam and Dean more permanently, and trying to learn more about the ways that humans live, considering their lives are largely governed by free will. Castiel begins to think and act for himself, and he proves one of the funniest and best parts of the show that remains by Sam and Dean’s side to the end.

10 “Hey, Assbutt!”

Throughout season 5, Castiel learns a lot from the Winchester boys, and he begins to adopt some of their language and attitudes into his character. However, having lived an eternity as an angel in Heaven, he struggles to adapt and use language appropriately or effectively. This is most clearly and humorously on display in the season 5 finale, “Swan Song.”

As Dean prepares to face Michael and Lucifer and get his brother back, Castiel steps up with the best of intentions to help his friend. With a holy oil Molotov cocktail in one hand, Cas calls out to the archangels with the most intimidating and intense insult he can imagine. “Hey, assbutt” certainly isn’t a typical insult, but Cas is new to using intense or offensive language, and like a child, he ends up combining words that make sense in his head to make something that is more laughable than confrontational.


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9 “Sam, Of Course, Is An Abomination.”

Jensen Ackles as Dean Winchester, Misha Collins as Castiel and Jared Padalecki as Sam in Supernatural

Earlier in that same season, Cas makes another social faux pas when speaking to Sam and Dean in an effort to make a plan of attack to kill an enemy. Cas retrieves a weapon that would be perfect for the job, but the catch is that it needs to be wielded by a true servant of heaven. This evidently creates a problem, as Cas has begun to turn his back on his former faith and home.

In addition, Dean refuses to do it as he does not agree with the corrupt dealings of the angels, and Cas bluntly states why Sam is ruled out in the above quote. This tactless approach to declaring Sam’s unworthiness is funny because Cas is completely innocent and sincere in his statement. However, the allusions are highly insulting, with Cas specifically referencing Sam’s demon blood, which was given to him against his will as a baby. But Cas is oblivious of his error.

8 Castiel Watching Explicit Content

Misha Collins as Castiel and Jared Padalecki as Sam Winchester in Supernatural

In Supernatural season 6, as Castiel begins to settle more into his life as a fallen angel, he begins to investigate more aspects of mortal life. At one point, Cas is sitting in a hotel room with Sam and Dean, watching something intently on a screen with an inquisitive look on his face. Of course, he has questions, and with Sam and Dean nearby, he decides to voice his concerns about what is happening on screen.

Cas questions the implausible narrative playing out in what is evidently a pornographic film. Dean finds this unsettling and tells Cas to turn it off, adding that it’s weird to sit in a room of guys, and it’s weirder to talk about it. Then, a moment later, when the boys are joined by their maternal grandfather, Sam Campbell, Cas, innocently and naively, repeats the sage advice about not talking about, in a way that makes it seem like this is a regular occurrence.


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7 At The Liquor Store

Misha Collins As 2014 Castiel

Again in season 5, Castiel chooses to become more acquainted with the things he did not have access to as an angel in Heaven. When Cas is having a particularly stressful time with world ending events going on around him, he decides to take up drinking. However, with an angel’s constitution, this looks a little different to how others may process drinking alcohol.

Cas comes to Dean, slurring his words and appearing somewhat disgruntled. Dean recognizes something is wrong, and asks Cas if he is drunk, which Cas confirms he is. However, Cas then reveals that he visited a liquor store, and “drank it.” Whether Cas literally drank the entire contents of the shop is not shown, but his behavior certainly indicates he is heavily drunk.

6 Interrogating The Cat

Castiel going to interrogate the cat

A few seasons later, Cas has settled into life with Sam and Dean, and has a greater awareness of how humans behave. While he is much more stable and clear minded, he does still make significant errors in judgment as the gaps in his knowledge are slowly filling in through his lived experience. After all, Cas was like a child with a very basic understanding of humanity and life on Earth when he first arrived in season 4.

In Supernatural season 8, one of these gaps in his knowledge makes for a hilarious interaction with a cat in a small town. Cas and the boys investigate a recent robbery in an elderly care home. While they all split up to cover more ground, Cas takes a passing comment from one of the women as a major tip. In an effort to be helpful, he volunteers to interrogate the cat that she mentions, but this is obviously an exercise in futility. Regardless, Cas puts in work trying to crack the confession from the cat, but it’s to no avail.


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5 Cas Undercover

Castiel shows off an FBI badge

In season 10, Cas is given a lot more trust in interviewing possible witnesses and speaking to people. His knowledge and skills have come a long way, and Dean chooses to tag Cas in on a job where they impersonate FBI agents using fake badges. This is a big moment for Cas, but it doesn’t go without a hitch, as Cas continues to make minor errors.

In what becomes one of his most iconic and memable moments, Cas introduces himself with the badge in hand, but holds it upside down. This is an obvious mistake, but not one that goes unnoticed by the people they speak with. However, in the final season, Cas has a moment to redeem his earlier mistake when he and Jack pretend to be FBI and Jack is the one to hold the badge upside down. At least he wasn’t the only one who made the mistake.

4 Booping Kevin Tran

Kevin Tran becomes a ghost in Supernatural.

Towards the end of season 7, Cas was dealing with some major monsters. The leviathans were creating problems for the boys, and Cas managed to fight them back at a great personal cost. Through their conflicts, Cas became significantly less coherent. Fortunately, he was still able to remember some of the more important tasks he needed to perform, but he was in a compromised condition that made him act in strange ways.

He asked the boys to pull his finger when he first saw them, praised the demon Meg for her beauty, despite their tenuous relationship, and booped the young prophet, Kevin Tran, on the nose. All of this was out of character, and as traumatic as it may have been, it was also entertaining to see Cas acting so loose when he had typically been much more uptight. He eventually finds a way to heal, but loopy Cas was a barrel of laughs while he remained on the show.


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3 Steve At The Gas N Sip

Human Castiel making coffee in Supernatural

Early in Supernatural season 9, Castiel is struggling with the loss of his grace, which leaves him human. As a human, Cas has an opportunity to finally experience humanity on a completely different level than anything that came before. Cas accepts his new life, and chooses to pursue a normal life.

This normal life leads Cas to take on a new identity as a man named Steve. Steve gets a job as a sales associate at a Gas N Sip, and he seems to enjoy his new life. However, even as a human, Cas still manages to display his unique sense of humor and comedy stylings. He faces some regular struggles as a human, but his unique approach and his bright attitude make it a fun and engaging story thread.

2 Getting The Fruit From The Tree Of Life

Dean, Castiel, and Sam Look Worried Next to an Energy Portal in Supernatural

Even as the series neared its end in season 13, Castiel still proved to be one of the funniest and most useful characters on the show. As an angel, he has numerous powers that make him an astonishingly good fighter, he can teleport, and he can heal people. However, despite his magnificent powers, he still manages to be awkward and hilarious in every situation.

As another world ending event looms near, Cas is assigned to recover a special artifact that could help save the world. The fruit of the Tree of Life is heavily guarded, but it could be the key to saving the world. With such a dangerous mission, Cas is clearly the man for the job. So, he is sent to recover the fruit, but upon returning, he reveals that he took out an army of Djinn, and potentially agreed to marry their queen to end the conflict.


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1 “Wookie?” – Season 9

Dean and Castiel help prepare Crowley to posess Sam in order to force Gadreel out of Sam's body in Supernatural

However, one of the best and funniest moments from Cas comes in season 9, in a moment that shows he has learned a lot in his time on Earth and finally gets references. From the moment Cas arrived on the show, he struggled with the boys making references to music, films and other parts of popular culture. Cas is working with other angels in order to stop Metatron from taking over heaven. When he and Gadreel arrive at a guarded gate, Gadreel asks how they can get in undetected, to which Cas raises a pair of handcuffs and simply says “Wookie?.”

Now, while this may not be exactly how someone would reference the moment in Star Wars when Han and Chewbacca sneak past stormtroopers by pretending Chewie is a prisoner in cuffs and Han is a guard, it’s a reference. Gadreel has no idea what Cas means, which is a hilarious twist from the earlier moments, and a highlight for Cas. All of this combines to showcase how much of a fun and engaging character Cas is from his first appearance on Supernatural, through to the end.

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