Eldon Dedini spent decades drawing for Playboy and The New Yorker, filling his panels with satyrs, nymphs, and businessmen caught in absurd domestic and mythological scrapes. This film traces his career from magazine cartoonist to one of the most recognized names in American gag cartooning, using his own artwork, archival material, and interviews with people who knew his work to build a portrait of a life spent at the drawing board. It follows him through the postwar boom in magazine cartooning, when Playboy and The New Yorker were competing for the sharpest satirical pens in the country, and looks at how his loose, painterly style set him apart from flatter editorial cartooning of the era. The film stays close to the work itself, treating each cartoon as a small piece of evidence about how Dedini saw the world, right up to the end of a career that ran for more than fifty years.