When Supernatural introduced angels into the lore in season four, many thought these were the good guys to counterbalance all the demons. Yet, as it turns out, angels are just "dicks with wings," as Dean Winchester put it. From archangels to seraphim to Nephilim, angels are not the saviors the show's heroes were hoping they'd be.

Even Team Free Will's own Castiel has had terrible moments throughout the series. While some angels commit horrible acts out of a sense of superiority to humans, others do bad things with good intentions. Here are the 10 most evil angels in Supernatural.

RELATED: Supernatural: 10 Times Dean Didn’t Deserve Castiel’s Friendship

Billie

 Billie as Death talking to the brothers in Supernatural

After Death is killed, Billie, once a reaper in Nebraska, takes on the mantle of Death. She grows tired of the Winchesters and the countless chances at life they are given, so she threatens to throw them into the Empty the next time they die.

In another battle where Sam dies, Dean overdoses to meet Billie in person and beg for the return of his baby brother. He even tries to persuade her that Sam is the only one that can stop the Darkness from destroying the world, but she still refuses.

Zachariah

Zachariah threatens Dean while keeping him captive in Supernatural

When the Winchesters resisted saying yes to their archangel counterparts to set off the apocalypse Zachariah took it upon himself to intervene and do everything in his power to get the brothers on board. He started by placing Sam and Dean in a real haunting situation, but without their previous expertise and knowledge to prove they were born to do this.

His cheerful boss demeanor turned sour when they refused to follow the divine plan. Zachariah resorted to hunting Sam and Dean in Heaven when they died again.

Lucifer

Fans thought they'd seen the last of Lucifer when Sam jumped with him back in the cage at the end of season five, but the writers brought him back in season 11. When the Darkness was released, it broke his cage and allowed him to make a psychic connection with Sam. He used it to his advantage to torture the younger Winchester.

His possession of the beloved Castiel though made him a truly vile villain. Using their best friend to torture the Winchesters is a move straight out of The Bad Place.

Gadreel

God locked up Gadreel in the darkest corner of Heaven after he let the Serpent into the garden. When the angels got kicked out of Heaven after the Winchesters' perform the tablet trials, Gadreel took his second chance by starting with a lie and calling himself Ezekiel.

He then took advantage of Dean's desperation to save Sam and possessed Sam, promising to release him once he was healed. Instead, he used Sam's body to kill Kevin Tran and follow Metatron as Heaven's new second in command.

RELATED: Supernatural: 10 Demons That Are Stronger Than Angels

Metatron

Metatron in Supernatural

The Scribe of God felt a greater fondness for humans than his own species, but he tricked Sam and Dean into banishing all the angels from Heaven with a trial from the tablets. He convinced the fallen angel Gadreel to join him in his endeavor to rebuild Heaven, leaving Sam vulnerable and out of control of his body.

Metatron was a master manipulator and pulled the strings on his puppets to get what he wanted. He even went so far as to stab and mortally wound Dean. When Castiel imprisoned him, he threatened to kill everyone upon his release.

Naomi

Naomi in Supernatural

The leader of one of Heaven's factions used Castiel to spy on the Winchesters for her and wiped his memory every time he returned. She programmed him to kill Dean by having him murder hundreds of clones of the older Winchester so that he could accomplish his mission of retrieving the angel tablet.

When Samandriel revealed the location of a tablet, she forced Castiel to kill him. Naomi insisted she could be trusted but proved over and over that she was as ruthless as her brothers and sisters in the war for Heaven.

Uriel

Uriel looking at Dean in Supernatural

Once Castiel's partner and fellow soldier in the trenches, Uriel gave in to his darker tendencies in the name of Heaven. He blindly obeyed orders to kill Anna and when the Winchesters got in the way, he was prepared to kill them, too. He secretly recruited angels like him who wanted Lucifer's release to start the apocalypse.

When Castiel found out about his plans, Uriel tried to kill Castiel as well. Even a younger version of himself that Anna recruits, when she travels back in time, is ready to kill without a second thought.

RELATED: Supernatural: 10 Continuity Errors Most Fans Missed

Anael (a.k.a. Sister Jo)

An image of Sister Jo looking surprised in Supernatural

When the Fall happened, Anael didn't desperately choose any vessel. She listened for prayers and carefully chose a woman whose husband was dying. She made a trade to save him for the woman's body. After that, she became a faith healer named Sister Jo who traveled the country performing miracles for payment so that she could live a lavish life on Earth.

When Lucifer returned, she made a deal with him and became his right-hand woman. She fought the Winchesters for him and helped Lucifer gain the throne in Heaven.

Bartholomew

Bartholomew in Supernatural

Naomi's protege only lasted for three episodes, but in his short time on the series Bartholomew wreaked havoc. He posed as a televangelist named Reverend Buddy Boyle to recruit humans who would serve as angelic vessels. But the problem was that not all humans could handle the divine power and many exploded into bloody pieces.

Their deaths were inconsequential to Bartholomew. His greed and desire for power led him to hunt down a peaceful faction of angels who wanted no part in any more wars.

Apocalypse World Michael

Season 13 brought forth an alternate reality where Lucifer and Michael battled it out and Michael won. But this Michael became twisted and cruel, creating an Apocalypse World that he ruled as a dictator. When he learned of the other reality where the Winchesters still live and the world didn't end, this version of Michael planned to lead an invasion to kill the humans of the Winchesters' world.

After a failed battle, he tricked Dean to let him use his body to stop their world's Lucifer. Instead, he used Dean as his true vessel to destroy their world.

NEXT: Supernatural: 5 Characters Who Were Killed Off Too Soon (& 5 Who Didn't Die Soon Enough)