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"Plucky Pennywhistle's Magic Menagerie"

Sam and Dean investigate a case in Wichita involving a man who was killed by an octopus on dry land. They soon discover that childhood fears are coming to life, and that a children's pizza place is the center of the phenomena.

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Season 9,Episode 16 -"Blade Runners" - Dean is frustrated when he can't reach Crowley who has promised to find The First Blade. When Crowley finally calls Sam and Dean, he tells them he fell off the wagon and has been injecting human blood and needs their help. To make matters worse, he had a demon helping him find blood, but she sold him out and told Abaddon that he and the Winchesters were searching for The First Blade. The brothers need to find the blade before Abaddon does, so they enlist the help of a former member of the Men of Letters.

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Season 9,Episode 17 -"Mother's Little Helper" - Dean struggles with the after effects of the Mark of Cain. Meanwhile, Sam hears about a case where straight-laced people are turning into violent murderers. Sam suspects possession and suggests to Dean that they investigate, but Dean tells him to go without him. While interviewing the local townsfolk, Sam meets an elderly woman named Julia, who tells him the Men of Letters came to town in 1958. Josie tells Sam the story of a young man named Henry Winchester and his female companion, Josie Sands. While Sam is away, Crowley tests Dean.

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Season 9 Episode 18 -"Meta Fiction" -Metatron attempts to get Castiel to join forces with him. Still furious with Metatron, Castiel refuses, which sets a surprising plan in motion. Meanwhile, Sam and Dean capture Gadreel.

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Season 9 Episode 19 -"Alex Annie Alexis Ann" - Sheriff Mills calls Sam and Dean after she kills a vampire who attacked a prisoner named Annie. They discover Annie was kidnapped by a family of vampires who use her as bait to lure in humans they can then feed on. Sheriff Mills tries to rescue Annie from her captors, but finds out the hard way that family always comes first.

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Season 9, Episode 20 -"Bloodlines" - Sam and Dean investigate a case in Chicago, where they discover that various mafia-esque monster families are, unknown to humans, running the underbelly of Chicago. One is a family of shapeshifters run by Margo Lassiter, whose leadership is thrown into question when her brother David returns home. The other reigning family in town is made up of werewolves, lead by Julian Duval. While in Chicago, Sam and Dean meet Ennis, a man with a personal vendetta against the monsters. The Winchesters warn Ennis about heading into the hunter lifestyle, but Ennis refuses to listen and starts down a dangerous path.

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Season 9, Episode 21 -"King of the Damned" - Castiel captures one of Metatron's angels and asks Sam and Dean for help with the interrogation. Dean eagerly accepts, which doesn't go unnoticed by Sam. Meanwhile, Abaddon demands Crowley help her kill Sam and Dean. When he refuses, she reveals her shocking bargaining chip. Also, Castiel sets a meeting with Gadreel.

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Season 9, Episode 22 -"Stairway to Heaven" - After a massive attack on the angels, Castiel (Calls Sam and Dean for help. As they leave, Dean's eagerness to bring the First Blade doesn't go unnoticed by Sam who is worried about the cost to his brother whenever he uses the Blade. Meanwhile, Castiel is shocked when he learns the angel that caused the attack was one of his followers and did it in his name. Dean discovers there is a conspiracy amongst Castiel's angel followers and at the heart of it is Tessa, the Reaper.