The Story of Lando Freeman

Lando Freeman is voiced by Slink Johnson, a voice actor known for his later role as Lamar Davis in Grand Theft Auto V and for his work on other Adult Swim projects. The character's arrival as a mysterious handyman who claims family ties to the Freemans sets up a plot that explores themes of paternity, family legacy, and the burden of unexpected kinship — all filtered through the show's signature absurdist comedy.

Source: The Boondocks season 3 — Wikipedia (episode summary: "A new handyman in Woodcrest claims to be Granddad's long-lost son, Lando")

The episode parodies The Steve Wilkos Show, a syndicated daytime talk show that specialised in paternity tests, confrontations, and dramatic resolutions. Wilkos, a former Marine and former director of security for The Jerry Springer Show, built his programme around aggressive confrontations between guests. John DiMaggio — best known as the voice of Bender on Futurama — voices the Steve Wilkos parody, performing the host's characteristic intensity. The show is depicted as exploiting family conflicts for entertainment, a critique of the daytime talk-show industry that The Boondocks had previously explored in episodes like "The Trial of R. Kelly."

Source: The Boondocks season 3 — Wikipedia (episode notes: parody of The Steve Wilkos Show)

Samuel L. Jackson returns as Gin Rummy, a role he originated earlier in the series as a friend and gambling partner of Granddad. Jackson, one of the most recognisable actors in Hollywood with films including Pulp Fiction, Jackie Brown, and his many collaborations with director Quentin Tarantino, brings his distinctive voice to the recurring character. Billy Dee Williams, the iconic actor known for his role as Lando Calrissian in the Star Wars franchise, voices a fictionalised version of himself. The episode title — "The Story of Lando Freeman" — is a pun on Williams's Star Wars character, and his appearance as himself on the talk show adds a meta-textual layer to the paternity plot.

Source: The Boondocks season 3 — Wikipedia (guest star listing: Samuel L. Jackson, Billy Dee Williams)

John DiMaggio, the prolific voice actor best known as Bender on Futurama, Jake the Dog on Adventure Time, and numerous roles in video games and animation, voices the Steve Wilkos parody host. DiMaggio's gravelly, aggressive vocal delivery is well-suited to the parody of Wilkos's confrontational hosting style. The casting continues The Boondocks' tradition of drawing voice talent from across the animation and live-action worlds.

Source: The Boondocks season 3 — Wikipedia (guest star listing: John DiMaggio as Steve Wilkos)

Sung Dae Kang directed this episode with a production code of 312, placing it in the later portion of the season's production run. Aaron McGruder wrote the story and teleplay. The episode aired on July 4, 2010 — Independence Day — which adds a layer of ironic coincidence to an episode about family, identity, and the quest for paternal truth in the Freeman household.

Source: The Boondocks season 3 — Wikipedia (episode credits, production code 312)

The paternity storyline expands on the show's established background for Robert "Granddad" Freeman. Throughout the series, Granddad is portrayed as the reluctant guardian of Huey and Riley, children he did not plan to raise. The sudden appearance of a potential adult son introduces questions about Granddad's life before he took custody of his grandsons — a period the series rarely explores. The talk-show format allows the episode to resolve the paternity question while satirising the public airing of private family matters.

Source: The Boondocks season 3 — Wikipedia (episode summary)