It's a Black President, Huey Freeman

The episode is framed as a faux-documentary, with acclaimed German filmmaker Werner Herzog serving as narrator and interviewer. Herzog, known for his distinctive narration style in films such as Grizzly Man (2005), Fitzcarraldo (1982), and Aguirre, the Wrath of God (1972), voices himself — lending an air of grave anthropological seriousness to the absurdity of the Freemans' suburban lives. The choice of Herzog, rather than a conventional documentary narrator, signals that the episode treats the 2008 election as a subject of epic, almost surreal importance. Herzog's deadpan delivery of lines about Uncle Ruckus and Thugnificent's reactions heightens the satire.

Source: The Boondocks season 3 — Wikipedia (episode summary: "Werner Herzog follows the Freeman family...")

The episode chronicles the period from the 2008 election on November 4, 2008, through the inauguration of Barack Obama on January 20, 2009. Obama's election as the first African American president was a historic milestone that The Boondocks — a show built on Black political commentary — could not ignore. The episode aired on May 2, 2010, over a year after Obama took office, giving the writers time to observe the cultural reactions and satirise the way Obama's presidency was experienced by different segments of the Black community and the broader public.

Source: The Boondocks season 3 — Wikipedia (episode summary: "2008 United States presidential election to the inauguration of America's first black president")

The range of character reactions is the episode's structural device. Huey's indifference reflects his revolutionary political outlook — a Black president within the existing system does not represent fundamental change. Robert and Riley's enthusiasm represents the mainstream Black community's pride and hope. Tom DuBois's anxiety about his wife Sarah's sexual attraction to Obama is a satirical take on the Obama-as-sex-symbol phenomenon that circulated in popular culture during the 2008 campaign. Each character's response reveals their personality and political perspective more deeply than any conventional plot could.

Source: The Boondocks season 3 — Wikipedia (episode summary: character reactions described in the synopsis)

Political comedian and talk-show host Bill Maher, whose HBO series Real Time with Bill Maher was a prominent venue for political commentary during the Obama era, appears as himself. Maher's brand of liberal political satire aligns with the show's own perspective on many issues, and his cameo positions him as a voice of secular, rational commentary amid the chaos of Woodcrest's reactions. Maher's presence also reflects the real-world media ecosystem through which the Obama election was covered and debated.

Source: The Boondocks season 3 — Wikipedia (guest star listing: Bill Maher as himself)

Uncle Ruckus, the self-hating Black character who believes he is afflicted with "the Negro condition" and worships whiteness, reacts to Obama's election with characteristic bigotry. Ruckus's commentary on Obama satirises the real-world phenomenon of Black conservatives and self-hating figures who opposed Obama on racial grounds. Throughout the episode, Ruckus's views are treated as the most extreme and absurd position, but the show refuses to simply dismiss them — instead holding them up as the logical endpoint of the self-hatred the character represents.

Source: The Boondocks season 3 — Wikipedia (episode summary: "Uncle Ruckus contributes his critical racist antics")

Season 3 premiered on May 2, 2010, after a hiatus of over two years — the previous season had concluded in March 2008. The long gap heightened anticipation and made the season premiere an event. The episode is production code 304, directed by Sung Dae Kang and written by series creator Aaron McGruder. It marked the return of the show's signature political satire at a moment when American politics had been transformed by Obama's election, giving the writers a rich new vein of material.

Source: The Boondocks season 3 — Wikipedia (episode credits: directed by Sung Dae Kang, written by Aaron McGruder, prod. code 304)