Hugh M. Hefner's legacy of enduring free speech and free press values is embodied in the Hugh M. Hefner First Amendment Awards, established in 1979, which honor leading First Amendment scholars and advocates. Hefner also had a lifelong interest in film censorship issues and supported teaching about them at the University of Southern California for 20 years. His deep commitment to these values was confirmed when the author was granted unrestricted access to over 3,000 personal scrapbooks, which Hefner had kept in order to track free speech and press issues during his lifetime.

The format of the book is an homage to the in-depth conversational interviews Hefner pioneered as the editor and publisher of Playboy magazine. Stuart Brotman conducted in-person conversations with eight persons who in their lifetimes have come to represent a "greatest generation" of free speech and free press scholars and advocates. Notably, these conversations include:

Geoffrey R. Stone
Floyd Abrams
Nadine Strossen
Burt Neuborne
David D. Cole
Lucy A. Dalglish
Bob Corn-Revere
Rick Jewell