In 1924, Hirschfeld traveled to Paris and London, where he studied painting, drawing and sculpture. When he returned to the United States, a friend, fabled Broadway press agent Richard Maney, showed one of Hirschfeld’s drawings to an editor at the New York Herald Tribune, which got Hirschfeld commissions for that newspaper and then, later, The New York Times.

Hirschfeld started young and continued drawing to the end of his life, thus chronicling nearly all the major entertainment figures of the 20th century. During his eight-decade career, he gained fame by illustrating the actors, singers, and dancers of various Broadway plays, which would appear in advance in The New York Times to herald the play’s opening. Though the theater was his best-known field of interest, according to Hirschfeld’s art dealer Margo Feiden, he actually drew more for the movies than he did for live plays. “By the ripe old age of 17, while his contemporaries were learning how to sharpen pencils, Hirschfeld became an art director at Selznick Pictures. He held the position for about four years, and then in 1924 Hirschfeld moved to Paris to work and lead the Bohemian life. Hirschfeld also grew a beard, necessitated by the exigencies of living in a cold water flat. This he retained for the next 75 years, presumably because “you never know when your oil burner will go on the fritz.”

In 1941, Hyperion Books published Harlem As Seen By Hirschfeld, with text by William Saroyan.

Following a divorce from Florence Ruth Hobby, in 1943, he married Broadway actress/performer Dolly Haas. Haas died from ovarian cancer in 1994, aged 84. They had one child, a daughter, Nina (b. 1945).

In 1943, Hirschfeld married one of Europe’s most famous actresses, Dolly Haas. They were married for more than 50 years and had a daughter, Nina.

He was commissioned by CBS to illustrate a preview magazine featuring the network’s new TV programming in fall 1963. One of the programs was Candid Camera, and Hirschfeld’s caricature of the show’s host Allen Funt outraged Funt so much he threatened to leave the network if the magazine were issued. Hirschfeld prepared a slightly different likeness, perhaps more flattering, but he and the network pointed out to Funt that the artwork prepared for newspapers and some other print media had been long in preparation and it was too late to withdraw it. Funt relented but insisted that what could be changed would have to be. Newsweek ran a squib on the controversy.

In his 1966 anthology The World of Hirschfeld, he included a drawing of Nina which he titled “Nina’s Revenge.” That drawing contained no NINAs. There were, however, two ALs and two DOLLYs (“the names of her wayward parents”).

In Hirschfeld’s book Show Business is No Business, Feiden recounts the following story to illustrate what Hirschfeld meant when he referred to the “NINA counting” as a harmless insanity: “The NINA-counting mania was well illuminated when in 1973 an NYU student kept coming back to my Gallery to stare at the same drawing each day for more than a week. The drawing was Hirschfeld’s whimsical portrayal of New York’s Central Park. When curiosity finally got the best of me, I asked, ‘What is so riveting about that one drawing that keeps you here for hours, day after day?’ She answered that she had found only 11 of 39 NINAs and would not give up until all were located. I replied that the ’39’ next to Hirschfeld’s signature was the year. Nina was born in 1945.”

In addition to Broadway and film, Hirschfeld also drew politicians, TV stars, and celebrities of all stripes from Cole Porter and the Nicholas Brothers to the cast of Star Trek: The Next Generation. He also caricatured jazz musicians— Glenn Miller, Duke Ellington, Count Basie, Dizzy Gillespie, Billie Holiday, and Ella Fitzgerald—and rockers The Beatles, Elvis Presley, Bruce Springsteen, Bob Dylan, Jerry Garcia, and Mick Jagger. In 1977 he drew the cover of Aerosmith’s Draw the Line album.

Hirschfeld collaborated with humorist S. J. Perelman on several publications, including Westward Ha! Or, Around the World in 80 Clichés, a satirical look at the duo’s travels on assignment for Holiday magazine. In 1991, the United States Postal Service commissioned him to draw a series of postage stamps commemorating famous American comedians. The collection included drawings of Stan Laurel, Oliver Hardy, Edgar Bergen (with Charlie McCarthy), Jack Benny, Fanny Brice, Bud Abbott, and Lou Costello. He followed that with a collection of silent film stars including Rudolph Valentino, ZaSu Pitts and Buster Keaton. The Postal Service allowed him to include Nina’s name in his drawings, waiving their own rule forbidding hidden messages in United States stamp designs.

In 1996, he married Louise Kerz, a theatre historian.

In 2002, Al Hirschfeld was awarded the National Medal of Arts. He was an Honorary Member of the Salmagundi Club.

The Martin Beck Theatre, which opened November 11, 1924, at 302 West 45th Street, was renamed to become the Al Hirschfeld Theatre on June 21, 2003. It reopened on November 23, 2003, with a revival of the musical Wonderful Town. Hirschfeld was also honored with a star on the St. Louis Walk of Fame.

On January 20, 2003, Hirschfeld died of natural causes in his home at 122 East 95th Street in Manhattan. He was survived by his daughter Nina Hirschfeld West, and his third wife, Louise Kerz.