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."