Supernatural‘s Castiel cracks us up. Remember when he attempted to use voicemail? The member of the Heavenly Host has impressed us with both his accidental humor as well as his evolving kindness as he learns to appreciate humankind, what it means to have free will, and the important things in life in general. Cas’ goofy use of the human language, like his spontaneous attempt at swearing during a pivotal, tense scene, is so beloved that it’s the most-quoted lines in the series.

There have also been many times when Cas just made our jaws drop with his cruelty, his stupid decisions, and what he really thought was the right thing to do. He is like the old poem by Henry Wadsworth Longfellow: “There was a little girl who had a little curl right on the middle of her forehead. When she was good, she was very good indeed, but when she was bad she was horrid.

Castiel jumps from one extreme to another, yanking Dean up from Hell and sucker-punching the planet as a false god, showing us both the best and worst of what good intentions can bring.

Some will make you chuckle and some will make you cringe. Here are the 16 Worst Things Castiel Has Done.

16. He Took Away Lisa And Ben’s Memories Of Dean

Cindy Sampson as Lisa and Nicholas Elia as Ben in Supernatural Supernatural: 16 Worst Things Castiel Has Done

Lisa Braedon, the love of Dean Winchester’s life, lives a normal life with Dean for a while with her son, Ben. Due to their connection to Dean, they are threatened, ultimately kidnapped, possessed, and nearly killed by Crowley and his demons. Castiel saves a dying Lisa, but Dean also asks him to erase himself from her mind. When Castiel removed every memory that Lisa and Ben had of Dean Winchester, it seemed like the humane thing to do, but was it really?

Even though Dean begged him to do it, Cas should’ve known that it was the only way for Dean to really enjoy a normal life. It’s a tragedy that too many writers use: the necessary culling of a girlfriend, boyfriend, or family because the job is just “too dangerous.” Of course, the real reason writers do this is to keep the story interesting and the characters open for anything new, including relationships, which just seems lazy.

This all occurs during season six, of course, which is when we see Cas at some of his worst moments.

15. He Tried To Suck Up To Dean With Girly Mags And Pie

Castiel Supernatural Pie Supernatural: 16 Worst Things Castiel Has Done

It’s one of the most hilarious Castiel scenes ever written. It’s so famous that there are actual memes made from it. During season eight’s episode “The Clip Show”, Castiel finally reunites with the Winchesters after pissing Dean off and not trusting the brothers with the angel tablet. To make up with Dean, Cas heads to a convenience store and hilariously creates a sort of gift basket for his friend.

From porn to beer to beef jerky, Cas adds items that prove that he knows Dean very well. He awkwardly navigates the store, breaking an egg here, leaving a door open there. The attendant follows him around, wincing and exclaiming, “Dude!

Castiel even adds toilet paper, but it’s when he demands, “Where’s the pie?” that everyone loses it. When the young man tells him, “I think we’re out,” Cas grabs him and snarls, “You don’t understand. I need pie!” That’s dedication right there.

14. He Became Emmanuel Allen And Got Married

Castiel Daphne Allen Emmanuel Allen Supernatural: 16 Worst Things Castiel Has Done

It was like one of those Marvel “What If?” issues where you ponder what would happen if Castiel became human and got married – only it really happened. When Daphne Allen found Cas naked, wandering out without any memory of who he was or where he came from, in season seven’s “The Born-Again Identity”, her kind, open heart fell in love with him.

Plenty of fans can empathize, but Daphne, a woman of faith, believed him to be a gift from God. Hmm. Again, plenty of fans may agree.

In the span of a single episode, not only did they get married, but they also decided to offer healing services to broken souls once they learned that “Emmanuel” had the power to heal, which was actually Castiel’s angelic healing powers. Dean appeared and saved Daphne from a demon, only to immediately whisk her husband away.

13. Future Cas Organizes Orgies And Is Stoned All The Time

Castiel Future Supernatural Supernatural: 16 Worst Things Castiel Has Done

For an angel, Cas has engaged in some pretty devilish behavior throughout his life. When Dean traveled to the future in the season five episode, “The End”, Cas is prepping a group of women for an orgy while the Croatoan pandemic spreads across the nation.

This fun-loving and free-wheeling Cas embraces the end of the world as we know it with lots of sex and drugs, easily admitting to being stoned. He also lacks his angelic powers during this period, which helps explain why he might adopt a hedonistic lifestyle.

It’s not the only time Cas enjoys a little bit of romance. Remember the time in season six when he made out with the demon, Meg? He announced that he learned the kissing “from the pizza man,” referring to the porn he saw on Dean’s TV.

12. He Removed Sam’s Wall To Blackmail Dean

Sam Winchester Castiel Wall Removal Supernatural: 16 Worst Things Castiel Has Done

What do you do when your BFF just won’t let you open the doors to purgatory? You erase the brain-wall that is keeping his brother from endless pain and suffering, naturally. When Castiel was working with Crowley to open up purgatory, the Winchesters obviously had issues with his big plan.

To erect the biggest road block in front of the brothers without killing them in season six’s “The Man Who Knew Too Much”, Cas callously took down Sam’s brain-wall, which prevented him from going insane from his memories of being tortured in Hell.

With no wall to protect him, Sam went into a coma. Cas informs Dean that he’ll cure Sam only if Dean stays out of his way, knowing that is the hunter’s only weakness. Sam then has to deal with incredible pain and confrontations with himself while Dean and Bobby attempt to stop Cas and Crowley. Even once Sam is able to save himself and come to Dean’s aid, they are too late.

11. He Beat The Crap Out Of Dean

Castiel Beats Dean Up Supernatural: 16 Worst Things Castiel Has Done

When Castiel worked for Naomi against his will in season eight (more about that later), he worked to obtain the angel tablet for Heaven’s gain. He lied to the Winchesters about it and accompanied them to the crypt within a warehouse where the tablet is kept. Unable to grab it himself, he waited for Dean to remove the tablet, then demanded it. When Dean refused, Cas beat him to a pulp, breaking his wrist, and nearly killing him in the process.

While it was one of the worst times that Cas beat up his best friend, it certainly wasn’t the only time. Dean took an angel beating after he banished Cas in the episode “Point of No Return”. Cas, completely pissed off that Dean would allow Michael to use him as a vessel and go against him, took out all of his anger on Dean’s body, nearly killing him in the process.

It’s not nice to hit your friends, Cas. They must not teach angels the whole “keep your hands to yourself” rule in Heaven.

10. He Took Claire Novak As A Host, Forcing Her Dad To Let Him In Again

Supernatural Castiel Claire Novak Supernatural: 16 Worst Things Castiel Has Done

It’s one thing when a grown adult allows an angel to enter himself to use him as a vessel, but taking the body of a child is pretty reprehensible. The first time Castiel meets Claire Novak in the 20th episode of season four, “The Rapture”, he callously says, “I’m not your father.” She only sees the body of her dad, Jimmy, Castiel’s host, and it only adds insult to injury (or vice versa) when, once Jimmy is free, Cas uses Claire’s body to save both the Novaks and the Winchesters from demons.

Jimmy then begs Cas to enter back into his body – to save his daughter from a lifetime of angel servitude – rather than die and finally be at peace. This may save her temporarily, but after a childhood of foster care, it’s clear that Cas really ruined her life. The Winchesters eventually help Claire find a new home with Jody Mills, only for her to become a hunter like them in the process.

9. He Lost His Damn Mind

Castiel Meg Supernatural Crazy Season Seven Reading is Fundamental Bees Supernatural: 16 Worst Things Castiel Has Done

When Castiel lost his mind in season seven, ending up as a mental patient, fans weren’t sure whether to laugh or cry. After everything that happened since he opened the door to purgatory, tried to become God, and was taken over by the Leviathans, nobody could blame him for going a little bonkers.

Part of Castiel is still there when he wakes up in the hospital, remembering that he was an angel, but he’s definitely cracked. He tells the men to “Pull my finger,” and says of Meg, his caretaker, “Will you look at her? My caretaker. All that thorny pain. So beautiful.” It’s even revealed later that once released from the hospital, Castiel showed up on Dean’s Impala, naked and covered in bees.

We were also treated to some great Castiel lines while he wasn’t running on four cylinders: “How important is lipstick to you, Dean?

8. He Chose To Stay In Purgatory

Castiel Dean Winchester Supernatural Purgatory Supernatural: 16 Worst Things Castiel Has Done

Sure, some people talk about remaining in purgatory to atone for their sins, but who takes that literally? At the end of season seven when the brothers and Cas finally take down Dick Roman the Leviathan, Cas and Dean are sucked right into purgatory with him. This is pretty much akin to a police officer or district attorney going to jail only to be surrounded by the criminals they’ve sent there over the years.

Naturally anyone would want to escape this situation, but Castiel punishes himself for all of the wrongs that he committed over the previous two seasons by electing to stay there and paying for his crimes while Dean escaped with the vampire Benny.

Eventually he is rescued by a bunch of angels because it would be pretty boring for the show to just leave him there forever. Lots of angels lost their lives saving him. You know, given how many people die for the three main characters of the show, you have to wonder if they ultimately do much good at all.

7. He Was Forced to Kill Dean Thousands of Times

naomi castiel supernatural Supernatural: 16 Worst Things Castiel Has Done

When Castiel was rescued from purgatory by the angels, it wasn’t an altruistic mission of brothers saving brother. Instead, it was a calculated move by Naomi that not only tortured Castiel but pretty much every Dean fan alive. Naomi manipulates Cas, using him to spy on the Winchesters and attempt to steal the angel tablet, and Castiel doesn’t even remember the chats that they have in a weird, CIA-like segment of Heaven.

In order to get the tablet, Naomi knows that Cas will have to kill his BFF, Dean, and she trains him to kill him over and over again as practice. The opening of “Goodbye Stranger” tricks the viewer into thinking that he’s already done it until the camera pans out and we see that there are thousands of Dean bodies strewn all over the place. It’s season three’s “Mystery Spot” again, only much more gruesome and chilling since Dean is being murdered by his friend.

6. He Resurrected The Leviathans

Supernatural Quiz Leviathan Supernatural: 16 Worst Things Castiel Has Done

They say that the road to hell is paved with the best of intentions and that pretty much sums up what happened when Castiel opened up purgatory. Believing himself to be the best candidate to rule over mankind (and Heaven) with God out of the picture, Cas absorbed the 40 million souls sent to purgatory along with the ancient Leviathans, the oldest creatures known to man.

The Leviathans are a nasty bunch hell-bent on destroying Earth and really shouldn’t have been allowed access to the planet once again, but Castiel didn’t think his plan through very well.

Even once the souls are returned to purgatory, enough Leviathans hang onto Cas to take control of his body and force him to let them go into a body of water, destroying him in the process. Sure, Cas comes back, as he has done multiple times, but his actions destroyed even more lives while the Leviathans terrorized Earth for a season.

5. He Saved The Titanic Only To Kill The Passengers Again

titanic supernatural sam dean castiel e1500393028158 Supernatural: 16 Worst Things Castiel Has Done

Once Castiel had the power of 40 million souls, he became drunk with it, craving more and more power to be able to smite and rule like no one had ever smote or ruled before. He did the only thing a power-hungry angel filled with souls could do to get more power: he saved 50,000 more people… from the freaking Titanic.

It wasn’t bad enough that Cas played with history like this just for his personal gain, either. It had such an impact on the planet that Fate intervened, threatening to kill the Winchester brothers if Castiel refused to repair the rift in time. Even an evil, soul power drunk Castiel still has a weak spot for the Winchesters, so he re-killed every one of the souls to keep the brothers safe.

4. He Stole The Grace Of Other Angels

 Supernatural: 16 Worst Things Castiel Has Done

Without their Grace, angels lose their power and can become mortal. Stealing an angel’s grace is considered a terrible offense worthy of torture or even death, but after Metatron extracts Castiel’s grace in season eight, the ex-angel steals the grace of Theo, one of Malachi’s minion angels. It results in the death of Theo, who was done serving Malachi and hoping to serve Metatron instead.

Stealing Theo’s grace wasn’t even enough to keep Castiel in full angel operating status. Since the grace was stolen, it begins to “burn out,” harming Cas in the process. Crowley murders Adina in order to give her grace to Cas in season 10, but Castiel is able to get Metatron to reveal where his remaining grace is located in order to obtain it once again.

3. He Was Tricked By Metatron To Cast All Angels From Heaven

Supernatural Quiz Metatron Supernatural: 16 Worst Things Castiel Has Done

It’s another case of the good intentions blues. The angel scribe Metatron approaches Castiel with a plan to trap all of the angels in Heaven and close it up to stop all of the chaos and suffering, and finally force the angels to work together.

Cas falls for the ploy and engages in some seriously WTF acts to help Metatron perform the spell, including killing an angel for the first “ingredient” of the spell he hopes to cast to punish all of the angels. Seriously, he should’ve known better after Metatron asked him to do the first task.

In the end, Cas’s mistake in trusting Metatron cost him and the rest of the world dearly. Naomi was killed and all angels were instead kicked out of Heaven, Metatron was granted god-like powers, and Team Free Will had to contend with him as well as Abaddon throughout the season.

2. He Betrayed The Winchesters With Crowley

Supernatural Quiz Crowley Supernatural: 16 Worst Things Castiel Has Done

How could Castiel know that performing such heinous acts for Metatron could only lead to more hell on earth? Aside from the fact that it should be obvious, how about because he’d just learned that lesson the hard way, a couple of seasons prior, when he worked with Crowley to open up purgatory?

Not only did Cas constantly lie to and betray his best friends, but he also provided Crowley with monsters to experiment on, tortured people, and even killed his old friend, Balthazar.

Castiel never planned to work with Crowley forever. He betrayed him at the last minute, absorbing all of the soul power himself, but in the end the results still spoke for themselves. Had Crowley taken in half of those souls, it could’ve been worse, as he would have surely used them for nefarious purposes, but the situation may have also improved, since both of them would only contain half of the power.

1. He Tried To Be God And Killed A Ton Of People

Misha Collins as Castiel in Supernatural Supernatural: 16 Worst Things Castiel Has Done

During the entire sixth season, Cas became so secretive that Sam and Dean had no idea what the angel was up to only to discover too little, too late that he’d been working with Crowley. His ultimate purpose had been to make the world a better place, but in the end, he consumed so much power that he declared himself to be their new god and demanded that they bow down to him lest he smite them on the spot!

Although Cas’s power play in season seven’s “Meet the New Boss” may have resulted in countless deaths, pain and suffering, but it didn’t last very long. The Leviathans that he brought back from purgatory were too powerful to be contained and destroyed him. It’s a good thing that Dean held onto his trench coat, since he came back for it eventually. Think he’ll do it again next season?

Are there any misdeeds in Castiel’s Supernatural past that we forgot? Let us know in the comments!

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