Maccari was born in Siena.[1] At the age of 19, he enlisted and fought in World War I as an artillery officer.[1] Having returned to Siena in 1920, he graduated in law and started working at a legal practice in Colle di Val d'Elsa.[1] During these years, he began painting and etching.[1] In 1924, he also started working as a graphic designer for the weekly magazine Il Selvaggio (The Wild One),[2] and published his first graphic caricatures.[1]
Before and during World War II, Maccari worked for several other magazines as a journalist and author, and held fascist views;[1] he had taken part to the March on Rome of 1922 that led to the taking of power by the Italian fascist movement led by Benito Mussolini.[1] Maccari was also a set and costume designer.[1] From 1941 to 1975, he staged nine performances in Rome, Venice, Florence, Siena, Milan, and Spoleto.[1] After World War II, he continued to be a popular artist, and in 1962 was appointed president of the Accademia di San Luca in Rome,[1] where he died in 1989.[1]
In 1950, Giuochi e sports (Games and Sports), a book published in Turin, included illustrations by Maccari.[1] The chapter "Fencing" was written by Giani Stùparich, who had won the 1948 art competitions of the Olympic Games with a gold medal in literature;[1] the submitted drawing may have come from this book.[1] Maccari is also the real author of a quotation that is often misattributed to Winston Churchill and Ennio Flaiano ("In Italy, fascists divide themselves into two categories: fascists and antifascists"). Flaiano himself was in fact attributing it to Maccari.[3][4]