10.16 Paint It Black

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Title Paint It Black
Episode # Season 10, Episode 16
First aired March 25, 2015
Directed by John F. Showalter
Written by Brad Buckner
Eugenie Ross-Leming
On IMDB Paint It Black
Outline Sam and Dean investigate strange suicides and murders that are being committed by people who attend the same Catholic church.
Monster Vengeful Spirit
Location(s) Worcester, Massachusetts
Fall River, Massachusetts
Florence, Italy (1520)
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In a church in Worcester, MA, Terry Sloan is absolved of his sins by Father Delaney. A spirit watches Terry as he walks out of the confessional. Terry takes a candlestick with him. Outside the church he disembowels himself with the sharp end of the candlestick.

At his lair, Crowley is being berated by Rowena for not intervening with the Grand Coven on her behalf, so she would be allowed to practice real and powerful witchcraft again. She accuses him of helping the Winchesters and preferring them to his own flesh and blood. In a church basement, Sister Mathias is talking to Isabella about the man Isabella loved before she became a nun, telling her his name was Piero and he was a painter and that Isabella was his muse and posed for him.

In the church, Frank and Lisa McCarthy are watched by the spirit, as Frank leaves the confessional. Later in their home, Frank sighs about having to work such long hours. Lisa calls him a liar and stabs him with a pair of scissors. After he dies, a cloud of smoke leaves Lisa’s body and she starts screaming in horror.

Sam and Dean pose as FBI agents to investigate the case of Terry Sloan and two other suicides, all Catholics. They visit Father Delaney in the church to discuss the McCarthy murder, asking about Frank’s confession, but Father Delaney won’t reveal anything he said. He does confirm, however, that all the victims (all men) had recently been to confession. Father Delaney introduces Sister Mathias, Dean checks her out and they introduce themselves as agents Allman (Dean) and Betts (Sam). Sam goes to snoop around, leaving Dean with Sister Mathias. During their talk. she hints that Frank as well as an earlier victim were possibly cheating on their partners. Dean then questions Sister Mathias about her choice to become a nun, and why someone would choose to quit one life for something so different, to which Sister Mathias says she needed to find something larger than herself to focus on.

Leaving the church, Dean points out that the theme of the case seems to be guys doing their women wrong. Lisa had no idea Frank was cheating on her, however, so maybe she was controlled by someone who did. All the victims did go to confession, so Dean asks: ”Sammy, how long has it been since my last confession?”

In the church basement, Isabella tells Sister Mathias about her love and obsession for Piero. She posed for the painting that turned out to be his masterpiece – in Florence, Italy, in 1520. But when Isabella confessed her love to Piero, he said he loved another more – his art. Isabella fell into despair and was forced into the convent by her father. The things from her father’s estate are spread out on a table in the church basement, including Isabella’s journal.

Back at his lair, Crowley has decided to do something nice for his mother. He brings her Olivette, the high priestess of the Grand Coven, powerless in iron chains. Rowena slaps her around, but Olivette says it’s a useless endeavor because what Rowena is looking for no longer exists. ”The Coven is a pale relic of its past power,” all because of persecution engineered by the Men of Letters.

Dean enters the confessional with Father Delaney, and talks about how he was dishonest to ”Gina” and sometimes seeing two or three girls at the same time, rolling his eyes at his feigned remorse. Father Delaney gives him a standard penance and advises him to do some soul-searching. Dean turns serious and starts to talk about how he doesn’t feel ready to die. He always expected to go out pedal to the metal, but now that the end seems closer than he thought he confesses he wishes he could experience life in a different way from what he is used to. When Father Delaney asks Dean if he believes in God, Dean reply's with, "I believe there is a God. But I’m not sure he still believes in us."

The ghost of Isabella watches Dean exit the confessional, later possessing Father Delaney. In the church basement, Sister Mathias starts reading Isabella’s journal, where she reveals that her love for Piero had become hatred, and she snuck into his studio one night. She was about to smear red paint on his portrait of her, when she discovered him making love to another woman. Isabella stabbed Piero to death with a knife.

Sister Mathias tells Sam and Dean all about the ghost of Isabella, who started appearing when her family’s treasures arrived in the church three weeks earlier. Sister Mathias gives Isabella’s journal to Sam and tells them she was convicted of witchcraft and burned at the stake. Dean assumes her ghost is tied to the journal and tells Sam to burn it. Sam is reluctant – ”there might be more in here” – but Dean insists.

Dean and Sister Mathias begin searching the church, discussing how Isabella could have gotten around by possessing people, even though she was tethered to an object in the church. In the basement, Sam is reading Isabella’s journal, about the time when Piero was painting her portrait. He asked for some of her blood to mix into the pigment, but she cut off a piece of her own finger and offered it to him, asking him to grind it up and mix it all into the paint. ”I had completely become one with the painting and with Piero.” Sam closes the journal and starts looking for the painting in the basement. Up in the church, Dean finds Father Delaney gutted, and quickly tries to lead Sister Mathias to safety but she slaps him, sending him flying. Dean struggles with the possessed Sister Mathias, who pulls out a knife and tries to stab him. She says the priest had to die because his business was to forgive the unforgivable.

In the basement, Sam burns the painting, forcing Isabella’s spirit to leave Sister Mathias and burn away.

After a bit of torture in Crowley's dungeon Olivette tells Rowena about the Men of Letters, their bunkers around the world and that the only known surviving Men of Letters in the U.S. are Sam and Dean Winchester. Gotten all the information she cared to learned from Olivette, Rowena begins casting a spell to kill the high priestess. As Olivette begins to violently convulse, Rowena quickly puts a stop to the spell, realizing that death is an easy way out for Olivette, instead she turns her into a hamster and starts asking Crowley about Sam and Dean. But he quickly shoots her down: ”My relationship with the Winchesters is my business. I’ll handle them. I’m not killing them.”

In the Impala with Sam, Dean is incredulous about Isabella mixing part of her own body into paint. ”No woman’s ever done that for me.” Sam points out that Dean should be grateful Sam didn’t burn the journal as Dean told him to, since it held the answer. Sam tells Dean that he can always talk to him and that they will find a way to get rid of the Mark of Cain.




  • "Optimistic Background" by Peter Lea-Cox (APM Music)
(playing in the church as Terry Sloan confesses his sins)
  • "Scotland the Brave" by Ruth Connell
(hummed by Rowena while preparing to torture Olivette)
  • "At Rest" by Leslie Pearson (Bruton Music)
(playing in the church as Sam and Dean speak with Father Delaney and Sister Mathias; also played in 1.07 Hook Man)


Two-Faced Demon: Your mother remains... vexed with your highness, and vents her frustration by abusing the court. No one dares retaliate of course, and yes one expects to suffer in Hell. But I fear I have reached my limit, to wit [turns around to show a second face on the back of his head] I mean seriously.
Dean: I got a question, how does someone like you...

Sister Mathias: End up cloistered away from the world? Are you making fun of me Agent Allman?
Dean: No-no-no. I'm just wondering how somebody quits one life for something completely different, and then believe in it so much.
Sister Mathias: Well, in my case I felt I had no choice. My life had become painful, there was hopelessness. I felt I had to find something larger than myself to focus on. A kind of mission, I guess. You have no idea what I'm talking about I'm sure.

Dean: Don't be.
Dean: Tell me you didn't think that nun was hot, I think she had a little thing for me too.
Sam: Dean, she was married to Jesus.
Dean: Hiya Father.

Father Delaney: Pardon me?

Dean: Pardon you? I thought it was the other way around. So uh, I'm here to clean house, need to get some things off my chest.
Dean: It's the women father, where do I begin?

Father Delaney: Bless me father for I have sinned is usual.
Dean: Right good, yeah so that, and um. So this not something that I'm proud of, I let them think we have more of future than we do, you know. Ah, Gina.
Father Delaney: Gina?
Dean: Oh man, don't get me wrong I mean she was- it was good times; you mean you know how it is the sex and the lasagna, but I was not honest with her. Sometimes I as seeing two maybe three girls at the same time, sometimes in the same day. You get the picture. And it wasn't just Gina, it was endless. It's making me sick.
Father Delaney: And you wish to be forgiven my son?
Dean: I do I need to clean up my act.
Father Delaney: As penance you shall say five 'Hail Marys,' two 'Our Fathers,' and reflect on you transgression.
Dean: And then that's it, I'm good to go?

Father Delaney: One would hope some inner exploration will occur, the prayers are just the beginning to some serious soul searching.
Dean: What if I said I, I didn't want to die... yet. That I wasn't ready.

Father Delaney: Are you expecting to?
Dean: Always. The life I live, the work I do I pretty much just figured that's all there was to me, you know? Tear around and jam the key in the ignition and haul ass until I ran out of gas. I guess I just thought sooner or later I'd go out the same way I lived, pedal to the metal and that would be it.
Father Delaney: And now?
Dean: Now. Recent events made me think I might be closer to that than I really thought. And I don't know; there's things, there's people, feelings that I-I want to experience differently than I did before, or maybe even the first time.
Father Delaney: Go a little bit deeper perhaps, than with Gina?
Dean: Yeah. Yeah, I'm just starting to think there's more to it than I thought.
Father Delaney: Learning that there's more to the universe than your tiny world, can be a frightening discovery. Do you truly believe in God Agent? Because that can be a comfort.

Dean: I believe there is a God. But I'm not sure he believes in us.
Sister Mathias: I never mentioned her to you, because it didn't occur to me she was connected to the murders. Ever since I've been here I've come across restless spirits of all sorts, they're all kind of sad, harmless. And eventually the poor things go to their rest.

Sam: Wait a second, so you're just comfortable around ghosts?

Sister Mathias: As a spiritual person, I've accepted many planes of existence, and as I've said they've all been harmless.
Rowena: The Winchesters? Again with the Winchesters. Perpetually the Winchesters.
Dean: Who mixes their blood and bones into paint? No woman's ever done that for me.

Sam: Is this you thanking me for not doing what you told me to do?
Dean: You know if you had burned the journal we wouldn't have known how to kill her would we?

Sam: Yeah, you're welcome.
Sam: You know, you were in that confessional a long time... Look man I'm just saying, I'm your brother, Dean, if you ever need to talk about anything with anybody, you got someone right here next to you.

Dean: Okay.
Sam: I heard what Sister Mathias was saying about you know, hiding pain by taking on a mission, and I know that's what you're doing, that's fine I get it I'm for it too. But I don't buy for one second that the Mark is a terminal diagnosis; so don't go making peace with that Idea, there has to be a way, there will be a way, and we will find it, that's what we do. So believe that.
Dean: Okay, Sammy.
Sam: You wanna try that again like you mean it.

Dean: Okay.

Trivia & References

"Paint It Black" gets its title from the Rolling Stones song of the same name.
Dean and Sam use the aliases Agents Allman and Betts, a reference to Gregg Allman and Dickey Betts of The Allman Brothers Band.
The church Sam and Dean are investigating is named after St. Philomena, who is the patron saint of babies, infants, and youth. The actual church is St. Andrew's-Wesley United Church on Burrard Street in Vancouver. It is located opposite the Sheraton Hotel where the Supernatural Convention was held from 2009-2014. This same church was used in 2.13 Houses of the Holy.
The sign for St. Philomena's Church has the quote, "He Ain't Heavy, He's My Brother - The Hollies and Jesus." "He Ain't Heavy, He's My Brother" was a hit song for British pop/rock band The Hollies in 1969, as well as Neil Diamond in 1970.
Rowena: You see my son, the spawn you speak of is now the King of Hell -- total Cinderella story I'd say. And now you dearest Olivette are prisoner of the baddest of the bad, and his devoted Mommy.
A Cinderella story refers to when someone, or a sports team achieves sudden unexpected success, despite years of mediocrity.


Teryl Rothery, who played Olivette, previously played the Medical Examiner in 2.17 Heart.

Sides, Scripts & Transcripts