Fan CastingThe Boondocks (Season 5/2016)
by Sony Pictures Television
Story added by thejacobtremblayfan on May 1, 2025
After a lengthy hiatus, The Boondocks is back, and Woodcrest is about to get a whole lot more crowded – and complicated. Season 5 introduces a new dynamic to the Freeman household with the arrival of Robert Freeman's new wife, Jennifer Winfrey-Freeman, and her son, Elias. While Huey grapples with newfound allies and Riley continues his quest for street cred, Robert struggles to adjust to married life and the challenges of raising a stepson who's anything but ordinary.read more
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Fan Casting Roles for The Boondocks (Season 5/2016)
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Jennifer Winfrey-Freeman (Robert's New Wife)
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Maya Rudolph
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Robert Jebediah "Granddad" Freeman
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John Witherspoon
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Hiro Otomo
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Forrest Wheeler
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Elias Winfrey-Freeman (Jennifer's Son, Huey And Riley's Stepbrother)
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Joseph Gordon-Levitt
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Huey Freeman
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Regina King
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Riley Freeman
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Regina King
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Tom Dubois
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Cedric Yarbrough
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Michael Caeser
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Benjamin Flores Jr.
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Sarah Dubois
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Jill Talley
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Roxanne Serafino
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Jenny Slate
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Louis Serafino (Roxanne's Younger Brother, Riley's Best Friend)
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Joshua Rush
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Ashley Jackson
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Daniel Huttlestone
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Jazmine Dubois
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Cindy McPhearson
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Phil
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