He began taking classes at the Art Institute of Chicago when he was eleven, and adopted the "Herblock" signature in high school.

Late in his second year there he was hired‍—‌after submitting some cartoons he had done in high school and college for the Evanston News-Index‍—‌to replace the Chicago Daily News' departing editorial cartoonist.

Block moved to Cleveland in 1933 to become the staff cartoonist for Newspaper Enterprise Association, which distributed his cartoons nationally.

In the early 1950s, Senator Joseph McCarthy was a recurring target of Herblock's cartoons, one of which introduced the term McCarthyism.

In the following decade, he attacked the US war effort in Vietnam, causing President Johnson to drop his plans of awarding the cartoonist with a Presidential Medal of Freedom.

Some of Herblock's finest cartoons were those attacking the Nixon Administration during the Watergate Scandal, winning him his third Pulitzer Prize in 1979.

In the 1980s and 1990s, he satirized and criticized Presidents Reagan, George H. W. Bush, and Clinton in addition to taking on the issues of the day: Gun control; abortion; the influence of fundamentalist Christian groups on public policy; and the Dot Com bubble.

Stating that he never got tired of his work, Herblock continued as the 21st century began by lampooning newly elected president George W. Bush.

When Herb Block died in October 2001, he left $50 million with instructions to create a foundation to support charitable and educational programs that help promote and sustain the causes he championed during his 72 years of cartooning.

[14] According to its website, the Herb Block Foundation "is committed to defending the basic freedoms guaranteed all Americans, combating all forms of discrimination and prejudice and improving the conditions of the poor and underprivileged through the creation or support of charitable and educational programs with the same goals.

The documentary interviews Jon Stewart, Lewis Black, Tom Brokaw, Bob Woodward, Carl Bernstein, Jules Feiffer, Ted Koppel and Ben Bradlee as witnesses to Block's life, work and indelible contribution to American satire.