Born in Cedar Rapids, Iowa, Hershfield was the son of Jewish immigrants. He studied in Chicago at the Frank Holmes School of Illustration and the Chicago Art Institute, and his career began at age 14, drawing sports cartoons and his comic strip about a dog, Homeless Hector, for the Chicago Daily News in 1899. He headed West, drawing for the San Francisco Chronicle by 1907.
In 1909, he was hired by Arthur Brisbane to work for William Randolph Hearst's New York Evening Journal. He switched to the New York Graphicwhere he did If I'm Wrong, Sue Me!, and when the Graphic folded, he went to the New York Herald Tribune and drew Meyer the Buyer.
Ron Goulart, in Encyclopedia of American Comics, described the Hershfield approach to cartoon humor:
- Hershfield drew in a vigorous, primitive cartoon style, and was enormously fond of shading, crosshatching and other basic inking techniques. Occasionally, he favored collages and sometimes made fun of other artists styles. In 1910, he started Desperate Desmond, a humorous continuity strip burlesquing melodramas, dime novels, and fiction weeklies that went in for the hairbreadth rescue and gloating villain sort of material. In addition to the villainous, top-hatted Desmond, the strip featured the stalwart Claude Éclair and the put-upon blond heroine, Rosamond. Hershfield's enthusiastic kidding of this sort of cliffhanger hokum did little to sour the public on its conventions. However, within a few years, such motion picture serials as The Exploits of Elaine and The Perils of Pauline would be attracting audiences to movie houses by doing the stuff completely straight.
- In 1912, Hershfield switched heroes and introduced a new strip called Dauntless Durham of the U.S.A. Durham, a handsome, pipe-smoking combination of Sherlock Holmes,Nick Carter and Frank Merriwell, was the soul of honor and polite to a fault. The object of his affection was the beautiful Katrina. In 1914, Hershfield abandoned parody for a quieter sort of humor and created Abie the Agent. The strip continued until 1940 and dealt with contemporary Jewish life in a big city. Hershfield specialized in gags with a Yiddish flavor.
The character was animated in Abie Kabibble Outwitted a Rival (1917).
In the 1930s, Hershfield was in demand as a banquet toastmaster, averaging some 200 banquets and dinners annually. During his lifetime, he was toastmaster or emcee at an estimated 16,000 events, including charity affairs, dinners and stage benefits.
Involved in a legal battle with Hearst in 1933-35, Hershfield drew a Sunday half-page, According to Hoyle, for the New York Herald-Tribune during those years.
On March 11, 1938, he was signed to head the story department of MGM's cartoon studio. He later commented, "They were so glad to welcome me, the day I arrived they gave me a farewell dinner."
He entered radio with a program called One Man's Opinion, and Just after he brought Abie the Agent to an end in 1940, he became a well-known radio personality, telling jokes on Stop Me If You've Heard This One and Can You Top This? He was a frequent guest on early television shows during the 1950s.
Hershfield also was a columnist for the New York Daily Mirror. His books include Laugh Louder, Live Longer and Now I'll Tell One.