Carter describes the challenges he faced in the first two years at the magazine, and how he worked to align with the staff. He reveals the techniques he used to reinvent the magazine, despite the lack of any real plan out the outset. Carter also talks about the origins of Vanity's Fair's famous Oscar parties, as well as the magazine's iconic Hollywood issue. He describes how the parties grew over the years, and how they and the Hollywood issue became embedded in the culture.

Graydon Carter then describes his personal and working relationships with some of his biggest collaborators. He discusses working with Annie Leibovitz, Michael Hitchens, Michael Lewis, and Bryan Burrough. Carter also reveals how he decides on his cover subjects, and what key elements go into each decision. He talks about some of the most iconic covers over the years, and a couple he may regret, including the one featuring Paris Hilton.

Carter and Kelly also talk about Graydon's long relationship with Donald Trump. Carter describes his first impression of Trump, and how their relationship has gone south over the years.