Starting with his getting kicked out of Exeter, the film follows Plimpton as he joins The Paris Review as its first editor and the creation of the "Art of Fiction" series.

Plimpton also starts writing for Sports Illustrated, undertaking various participatory journalism attempts, including pitching against an all-star major league baseball line-up, including Willie Mays, taking the field as an NFL quarterback with the Detroit Lions and skating with the Boston Bruins as a goalie.

The film features Plimpton as principal narrator and interviews with Hugh Hefner, Robert F. Kennedy Jr., Mel Stuart, Walon Green, Philip Gourevitch, James Salter, Christopher Cerf, Jonathan Dee, Jay McInerney, Gay Talese, Peter Matthiessen, Ken Burns, Mike Milbury, Robert Silvers, Taylor Plimpton and James Lipton, amongst others.

Bean described the first pages of the notebook as, "a journal, him packing and getting on a plane to go to Detroit to join the Lions, it mimics, really closely, what became the first page of the book.”[4] Talking about the film in interviews to promote its theatrical release, the filmmakers said, "Making our movie was an adventure, and a wonderful one at that.

"[11] IndieWire said, "smartly constructed, using copious archival interviews to allow Plimpton to largely tell his own story, Bean and Poling's documentary is a brilliant example of creative biographical filmmaking.