The Boondocks - Season 2 - Eps 2: Tom, Sarah and Usher
While on a date with Tom Dubois, Sarah Dubois meets the singing sensation, Usher. Sarah starts being obsessed with Usher, and Tom begins to think Sarah is cheating on him. Sarah kicks Tom out of the house and Tom moves in with the Freemans. A pimp Named Slick Back returns in this episode to try to help Tom get Sarah back.
About The Boondocks

Title: The Boondocks
First Air Date: 2005-11-06
Last Air Date: 2014-06-23
Status: Ended
Rating: 8.154/10 (from 369 votes)
Language: EN
Seasons: 5
Total Episodes: 55
Network: Adult Swim
Genres: Action & Adventure, Comedy, Animation
Production Companies: Sony Pictures Television, Adelaide Productions, Rebel Base, Sony Pictures Animation
Synopsis
When Robert “Granddad” Freeman becomes legal guardian to his two grandsons, he moves from the tough south side of Chicago to the upscale neighborhood of Woodcrest (a.k.a. "The Boondocks") so he can enjoy his golden years in safety and comfort. But with Huey, a 10-year-old leftist revolutionary, and his eight-year-old misfit brother, Riley, suburbia is about to be shaken up.
Cast

Regina King
Huey Freeman / Riley Freeman (voice)

John Witherspoon
Robert Freeman (voice)

Cedric Yarbrough
Tom Dubois (voice)

Jill Talley
Sarah Dubois (voice)

Gary Anthony Williams
Uncle Ruckus (voice)

Gabby Soleil
Jazmine Dubois (voice)