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Tom, Sarah and Usher
In The Boondocks season 2, episode 2, "Tom, Sarah and Usher" (2007), Sarah DuBois becomes obsessed with singer Usher after meeting him during her anniversary dinner with Tom. Believing she is having an affair, a paranoid Tom is kicked out, moves in with the Freemans, and enlists A Pimp Named Slick Back for advice.
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The Fund Raiser
In The Boondocks season 3 episode "The Fund-Raiser" (2010), Riley Freeman starts a, aggressive, mob-style candy-selling business to make his own money after Grandad refuses an allowance. Parodying Scarface and Goodfellas, Riley recruits Jazmine, Cindy, and Ed Wuncler III, turning the school fundraiser into a profitable, cutthroat operation while ignoring Huey’s warnings
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S1 E3 Grandpa's Wild Ride
Huey Freeman initiates a hunger strike to boycott BET, protesting its content. He gains support from the opportunistic Reverend Rollo Goodlove (voiced by Cee-Lo Green), who uses the movement for self-promotion. The episode parodies BET executives and explores themes of media responsibility.
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S1 E4 Funeral Frenzy
Granddad auditions for a play by Winston Jerome, a parody of Tyler Perry, but gets entangled in a homo-erotic evangelical cult. While Riley insists on using "pause" to monitor Granddad's phrasing, Huey works to stop the cult-like influence, culminating in a showdown between Granddad and the playwright.
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