Hershfield was born in
Knoxville, Tennessee, one of five children of immigrants
Isadore Abraham Hershfield and
Ida Alshanetsky from
Kiev, Ukraine. While growing up in Chattanooga, TN, he taught himself to draw. In 1922, as its art director, he illustrated virtually the entire "Dynamo", the
Chattanooga High School annual the year he graduated. He left his family to move alone to New York City in the early 1920s, where he studied art at the
National Academy of Design and joined the
Art Students League. Initially, he supported himself as an employee in the "morgue", or clippings library of the
New York World and worked his way up to staff artist. In 1925, he worked his way to Europe twice on a freighter to hone his drawing and watercolor styles. In 1929, he began writing articles and drawing cartoons and caricatures of famous people appearing in the news for the
New York Times. These appeared in the political and theater pages as well as their
Sunday Magazine. Since the
New York Times and the
Chattanooga Times were both owned by Chattanoogan
Adolph Ochs, Leo was given the opportunity to work simultaneously on the staff of the
Chattanooga Times where he interviewed, wrote and illustrated a column entitled "
Chattanoogans in Gotham". In 1933, he married Mary Emma Hurst of
New Bern, North Carolina. She had moved to New York to become a fashion model and was a chorus line member of the "
Roxyettes", the forerunner of "
the Rockettes" performing at the then-
Roxy Theater before the show moved to
Rockefeller Center. In 1941, Hershfield illustrated his first book for humorist
H. Allen Smith titled
Lo, the Former Egyptian. Over the next 38 years, he would illustrate the covers and interiors of almost 60 books, including more for H. Allen Smith as well as
Vincent Price,
Groucho Marx and
Richard Armour. In 1942, they moved to
Alexandria, Virginia where Leo took the wartime job of Art Director for the
Office of War Information in Washington, DC. When the war ended, he became a full-time freelancer, illustrating publications such as ''
Reader's Digest,
The Saturday Evening Post (where he illustrated their "Letters to the Editor" column for 17 years) and Kiplinger's Changing Times, where he contributed art to 390 consecutive issues. He also worked with advertising agencies like Ketchum, MacLeod & Grove illustrating advertisements for their clients. During this time, he also became the "artist/correspondent" for the controversial PM''. He created vivid political cartoons on every monthly cover of
The Democratic Digest, the publication of the
Democratic National Committee from 1954 to 1961. Hershfield practiced his creativity in multiple media including pencil, pen and ink, watercolor, block printing, wood carving, metal sculpture and photography. He even designed and built children's toys and wrote and illustrated a children's book. ==Courtroom illustration==