6 chapters across the catalog
Archival audio from the 1960s features wealthy, middle-class Black residents in Los Angeles expressing concern over the "exodus" of Southern Black people moving to the city. The speakers describe the newcomers as a "social problem" and express embarrassment over being associated with them. The hosts compare this "Boule" mentality to the themes explored in the television show *The Fresh Prince of Bel-Air*.
The long-standing professional and personal history between Will Smith and Chris Rock is traced back to 1995. Rock appeared on *The Fresh Prince of Bel-Air* in drag and later co-starred with Jada Pinkett Smith in the *Madagascar* films. The hosts emphasize that these men are not strangers, with Rock having presented Smith with his first Grammy Award decades ago.
A 1997 Essence Awards clip shows Bill Cosby introducing Will Smith, effectively "passing the torch" of the family-friendly Black superstar. The hosts highlight the deep history between Smith, Cosby, and Chris Rock, who presented Smith with his first Grammy. They suggest that Smith was groomed to be the "Barack Obama of Hollywood."
Will Smith recounts how he went "broke, broke, broke" after his early rap success due to reckless spending and failing to pay the IRS. He describes the embarrassment of being famous but having to ride the bus. The hosts discuss how tax trouble is often used as a leverage mechanism by the industry to control young celebrities.
Will Smith tells the story of meeting producer Benny Medina at the *Arsenio Hall Show*, which led to an impromptu audition at Quincy Jones' house. The hosts identify Benny Medina as a "scammy" Hollywood figure and discuss the "Hollyweird" nature of these sudden discoveries. They note that Smith's first major acting role involved a controversial gay character in *Six Degrees of Separation*.
The hosts discuss the character of Carlton Banks as the "corny" foil to Will Smith's "cool" persona. They note how Alfonso Ribeiro became trapped in the role, similar to Wayne Brady's "safe" lane. They argue that Will Smith's slap was a desperate attempt to break out of this "safe" perception and demand respect as a "bad boy."
