|“||Forget it, you're stupid.||„|
|~ Anna insults a nurse at the mental ward|
|“||That's why the Apocalypse is coming. That's why the angels are losing. That's why we're all going to die!||„|
|~ Anna predicts that Heaven will lose the Apocalypse whilst at the hospital|
Anna Milton is a villainess appearing on the TV series Supernatural, portrayed by Julie McNiven.
Initially, Anna was an angel and was Castiel and Uriel's garrison leader, as well as Castiel's friend. She was posted to watch Earth for over two thousand years. However, Anna became disillusioned with her role. Years of waiting without an answer from God led her to believe He didn't exist, so she tore out her grace and fell from Heaven in what witnesses saw as a meteor shower. She created a new tree upon her fall and was reborn as a human.
Anna lived an unremarkable life, but she did have nightmares about her Father wanting her dead and how her siblings were going to kill her. She became suicidal and was placed in a mental asylum for saying the Apocalypse would begin and she could hear angels.
In "I Know What You Did Last Summer," Anna is in an asylum having nightmares about the end of the world. Castiel tells Sam and Dean that, if she can hear angels, then demons will go to any lengths to capture her to hear what Heaven is doing.
Anna is almost taken by a demon but escapes and meets Sam and Dean, who takes her to a barn, but then demons led by Alastair arrive and try to abduct her. Just then, Castiel and Uriel show up to kill her, because Heaven has had enough of her treachery.
In "Heaven and Hell," Anna remembers an essential angelic weakness, a special sigil can banish angels. With the help of a psychic, the Winchesters remind her of who she truly is and embark on a quest to retake her grace. They find where her grace hit, but discover it is gone (Uriel took it earlier to prevent Anna from regaining her powers).
While still human, Anna's relationship with Dean increases and the two have sex in the back of Dean's car. She also tells Dean the problems with Heaven, how angels simply answer orders and have never actually seen their Father. Anna surrenders to the angels; however, Castiel is reluctant to kill his former friend. Before they can carry on, however, Alastiar bursts in and a fight breaks out. Anna manages to steal back her grace from Uriel. Doing so destroys her body and the blast also destroys Alastair's vessel.
Anna returns in "On the Head of a Pin," appearing in her human form (she was able to call in a few favors to get her body recreated to act as her vessel). She comes to talk to Castiel, who is suffering from a conflict of allegiances, as his love of humanity (particularly Dean) is making him question a few orders. She recommends he join her, but Castiel angrily refuses and orders her to leave. Later, however, she saves him from Uriel and kills the traitorous angel.
In "The Rapture," Anna appears in the backseat of the Impala to talk to Sam and Dean, and they tell her that Castiel has been forcibly taken back to Heaven; she advises them not to trust angels anymore because they are planning something very bad and it will affect everyone.
In "When the Levee Breaks," Anna appears to Castiel and demands to know why he let Sam out of Bobby Singer's demon panic room. Castiel simply replies that Anna shouldn't have come, at which point two angels appear and capture Anna, taking her away to Heaven.
In "The Song Remains the Same," Anna manages to escape from Heaven and, desperate to stop the Apocalypse plans to kill Sam and scatter his atoms across the universe so Lucifer can't use him as his true vessel. Castiel refuses to let her, and not sure if she can take him in her weakened state, Anna travels back through time to the year 1978, intending to kill John and Mary Winchester so they won't be able to conceive Sam. With Castiel's help, Dean and Sam travel back to the same year and manage to thwart Anna's first attempt to kill their parents.
Anna summons Uriel for assistance and tricks him into believing that it is Sam and Dan who will kill him. The two angels track down the boys and their parents to their hideout. Uriel restrains Dean while Anna succeeds in killing Sam. Anna then advances on Mary and hesitates to apologize for what she believes must happen, only to be stopped by Michael, who is possessing John (who was thrown out the window moments earlier). Michael puts his hand on Anna and burns her to death, then sends Uriel away and, after a conversation with Dean, sends Sam, fully healed, back to the present along with Dean.
- Anna desired the Apocalypse to be derailed, which coincidentally was the same thing Sam and Dean wanted, but Anna's methods of doing so were more rash and cold and set her against her former allies.
- Anna's surname was a reference to the poet John Milton, who wrote Paradise Lost, which was an inspiration for Supernatural.
- One of her reasons for becoming human was to experience human emotions, and its ironic lust was one emotion she became obsessed by because she was originally an angel and meant to be like "a statue, cold, unfeeling, perfect in every way."