The second season of the animated television series, The Boondocks originally aired in the United States on Cartoon Network's late night programming block, Adult Swim. Season two started on October 8, 2007 with "...Or Die Trying" and ended with "The Story of Gangstalicious 2" on February 4, 2008. Although fifteen episodes were produced for season two, only thirteen aired in the United States. "The Hunger Strike" and "The Uncle Ruckus Reality Show" never aired in the U.S due to legal reasons. Although these episodes were never aired in U.S.A, they were aired in Canada and Latin America; and were also released on DVD and iTunes.
All fifteen episodes from season two were released completely uncensored on a three-disc DVD set in the United States on June 10, 2008. In addition all episodes from season two are available on iTunes.
Granddad, Huey, Riley and Jazmine must avoid guards after they sneak in to a theatre to watch Soul Plane 2: The Blackjacking.
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.
Two men are invading homes, and Riley and Granddad are refusing to speak to the police. It gets worse when Granddad's car, Dorothy, gets stolen by the robbers. If Riley and Granddad still refuse, worse things may be in store.
Huey has a dream of Stinkmeaner and Granddad says that he was a menace and he sent him to hell like he deserves. Stinkmeaner's spirit later inhabits Tom Dubois' body and goes looking for revenge against Granddad. Huey must stop him from killing Granddad.
The infamous rapper Thugnificent moves to the neighbourhood with his friends Macktastic and Flonominal, eventually leading to Granddad becoming annoyed with his new neighbours. Their feud inspires Thugnificent to create a diss-track called "Eff Granddad".
After many failed attempts at online dating, Granddad finally meets a beautiful woman named Luna… who just happens to be a psycho.
After much begging and pleading, Riley (Regina King) is initiated into his hero Thugnificent's Lethal Interjection crew. When a local bully jacks his "ice," Riley turns to Macktastic (Snoop Dogg), Flominal (Busta Rhymes) and Ed III (Charlie Murphy) for advice on how to retaliate.
Riley (Regina King) wreaks havoc when he joins Tom's (Cedric Yarbrough) youth basketball team. Everyone realizes how much of a team player Riley ISN'T as soon as he hits the court. Written by Aaron McGruder & Andre Brooks & Jason Van Veen
Jericho Freeman, Granddad's cousin, and his family, who were displaced by Hurricane Katrina, arrive at the Freeman's home looking for a place to stay. Granddad reluctantly allows the family to stay, but is soon trying to get rid of them.
Granddad takes a vacation, leaving the boys alone, but just who is in charge?
A teacher calls Riley a "nigga" in class, causing Robert to decide that he wants to sue for restitution.
Huey and Riley listen to different perspectives on the story of their ancestor Catcher Freeman.
Granddad worries about Riley's sexuality when he notices that he begins to dress and act like "in-the-closet" rapper, Gangstalicious.
Huey goes on a hunger strike in a boycott of BET, and receives some high-profile support from Reverend Rollo Goodlove, who may be more interested in his own self-promotion than any good intentions.
In the wake of Huey's failed protest against the network, BET's Harvard-educated programming chief, Weggie Rudlin, is moving ahead with his promise to create The Uncle Ruckus Reality Show.