A German documentary, narrated by Werner Herzog (as himself), follows the Freeman family during the election of Barack Obama, the country's first black president. The episode takes place in three time periods: the months leading up to the 2008 Presidential Election, the months before Obama's inauguration, and the present day, with Obama currently serving as President of the United States.
In the days leading up to the 2008 election, each of the main characters of the show express their opinions of Obama's campaign.
- Huey Freeman is indifferent towards Obama, expressing that he is now "retired" in his role as a "domestic terrorist", a reference to Obama's purported association with Weather Underground co-founder Bill Ayers.
- Riley Freeman supports Obama because "he black" and that he will give Riley the right to act any way he wants; he believes a black president isn't going to come down hard on a fellow black person.
- Granddad is, like Riley, fast to place Obama on a pedestal. He also sees it as a sign that all of his "hard work" as a "civil rights activist" has finally paid off. He places a picture of Obama on his wall in the place where a picture of Huey and Riley once resided.
- Thugnificent has no idea who Barack Obama is or what his political ambitions are. However, he sees that it may be time for him to become an activist standing up for African American rights. He changes his wardrobe to a more "grown-up" suit and tie look, begins wearing glasses to appear intellectual, and records a song with will.i.am called "Dick Ridin' Obama", as a message that he is an ardent follower of Obama. The narrator notes that Thugnificent is probably making this change to increase exposure for his rap career.
- Tom and Sarah Dubois are both campaigners for Obama, wearing "Obama Guy" and "Obama Girl" sweatshirts. While they are both fans of Obama, Sarah shows that she is a supporter of Obama for his perceived good looks as well as his platforms.
- Uncle Ruckus shows extreme disdain for an African-American presidential candidate. He is seen throwing bricks at a cardboard cutout of Obama and states that "Mr. Obama Husain" will only take his bricks from his cold, dead, hands.
An election night party is held at the Freeman's home, where everyone, except for Huey and Ruckus, are celebrating Obama's election as the first African-American President of the United States.
In the months leading up to the inauguration, each character and their opinions are revisited.
- Huey is still very indifferent towards Obama. His response of "Eh?" to the idea of Obama being elected President leads to him drawing the ire of a large crowd of black people. His "remark" leads to national protests against Huey, with protesters seen burning an effigy of him. Huey feels there is no room for himself in Obama's America and decides that it's time for him to leave America, in an operation he dubs "Exodus".
- Ruckus, in no way, wants to attend the inauguration. He'd love to go just to hurl a brick at Obama, but his arm isn't what it used to be. Ruckus agrees to be a part of Operation "Exodus", since "Ruckus's got the License" and "Huey has the gas money". The two will leave America and go their separate ways at the Canadian border.
- Granddad and Riley both are overjoyed with the new President-Elect. Granddad says that Obama is going to lower his taxes, that he will be against corporate bailouts , and that he will withdraw American troops from Afghanistan. Granddad writes a letter to Obama, asking for a VIP invite to the Inauguration and following Inaugural Ball, where he requests to be seated near Beyonce. "Obama" (so it is written in the letter) agrees, giving Granddad two VIP tickets for all of his years of civil rights work. He gives Riley his second ticket.
- Thugnificent, in his new "political activist" role, appears on a political debate television show hosted by Bill Maher. Thugnificent's intelligence in the Federal Government is challenged, to show that his activist role is just a front. He is humiliated when he cannot name the three branches of the Federal Government.
- The Dubois' are both planning to attend the inauguration, but only one ticket is secured for Sarah. A starstruck Sarah prepares to go to Washington DC, hoping to see Obama, who is obviously more of a sex symbol in her eyes. It is stated that Obama represents, in Sarah's eyes, a superior version of Tom.
On the day of the inauguration, Granddad and Riley never make it to their "VIP" section, as they find out that a great many other attendees also received "VIP" tickets. Granddad is shot with a taser. Riley screams in vain for Obama to save them. Ruckus is arrested under suspicion of terrorism as a closet full of bricks and cardboard cutouts of Obama are found at his home and thus, Huey never completes Operation Exodus because he couldn't get a ride.
The characters are revisited in the Present Day.
- Granddad now hates Obama, removing his Obama picture from the wall and returning the picture of Huey and Riley. He complains that Obama is going to raise his taxes and says that Obama's promises are just like his tickets: worthless; Granddad finishes with "good thing I didn't vote for his 'lying ass'". Note: President Obama' has increased taxes on the wealthy (those with an annual income of $250,000 or more), passed a multi-billion dollar bailout for economic stimulation, known as the Stimulus Package and has made plans to withdraw troops from Iraq rather than from Afghanistan, contrary to Robert's wishes (except the troops part).
- Riley dislikes Obama for not being a "real nigga".
- Sarah, still starstruck, talks about seeing the handsome Obama, while Tom shows that he's ready to move on.
- Thugnificent returns to his old habits of dress and speech, a sign that his "activist" days are over. He takes credit for getting Obama in office, but says it's time to go back to normal.
- Ruckus is not legally allowed to leave the country as per the conditions of his parole, but is able to state his displeasure toward Obama nonviolently.
- Huey remains indifferent towards Obama, again remarking that he is "retired".
- Thugnificent's initial response to Obama's first name is a reference to an interview that DMX did with XXL.
- Later in the episode, Granddad says "Don't tase me, bro!" to an armed security guard at Obama's inauguration before being tasered. (University of Florida Taser incident)
- The Dick Ridin' Obama song is a parody of the songs "Yes We Can" and "It's a New Day", by Will.I.Am. Thugnificent was featured in the video.
- After Obama's electoral victory is announced on TV, Sarah says that "for the first time in my life, I'm proud to be an American," a reference to a similar quote by Michelle Obama, speaking in Milwaukee, Wisconsin during the 2008 presidential campaign.
- Thugnificent says he will replace the word "Nigga" with "Obama" and "Bitches" with "Michelle," a reference to a similar statement made by Jim Jones.
- The title is a reference to the 1966 Peanuts special It's the Great Pumpkin, Charlie Brown. It is the second time a Peanuts animated special was referenced in a title- the first being "A Huey Freeman Christmas" (A Charlie Brown Christmas)
- When Granddad is exchanging the picture of Huey and Riley with one of Obama, a picture of the cast of The Warriors can be seen as well as a picture of economist Thomas Sowell.
- In the interviews of Huey in his room, a real picture of Malcolm X can be seen behind him.
- Tom and Sarah are shown wearing Obama Girl and Boy t-shirts. Sarah's shirt is in reference to the viral video and internet star Obama Girl.
- In the beginning where Huey is one of Obama's top friends on Myspace is a reference to when the rapper Jin became one of Obama's top Myspace friends after his song "Open Letter To Obama".
- Early in the episode, John McCain states that Huey is a boy that thinks "Jesus is black, Ronald Reagan is the devil, and the government is lying about 9/11." This is a reference to "The Garden Party", where Huey speaks those exact words to party guests in his dream. They were also the first words Huey spoke in the series.
- This is the second time in the series Huey has had to abort an 'operation' "because he couldn't get a ride". The first was in "The Passion of Reverend Ruckus".
- Uncle Ruckus has more precise aim with his brick throwing unlike Season 1 ("Return of the King"). Ironically, he decides not to throw a brick at Obama at the Inauguration because "his throwing arm isn't what it used to be".
- This is the second episode in the series in which Riley is shown as a graffiti artist.
- Huey shows Ruckus an outdated map from the Cold War era.