Gottlieb's career as a jazz photographer was largely limited to a decade spent as a jazz writer and editor in the 1940s. But his photographs—a tragic 1947 portrait of Holiday; an impossibly young Miles Davis in the studio with Parker; Thelonious Monk, shot from below, at the piano—remain among the most recognizable and frequently reproduced images in the history of jazz.

Born in Brooklyn, Gottlieb became a jazz fan while attending Lehigh University. After graduating, he went to work at the Washington Post, where he wrote a weekly jazz column; he began photographing musicians because the newspaper could not afford to send a photographer to accompany him to performances.

After serving in World War II, Gottlieb moved to New York and joined the staff of Down Beat magazine as an assistant editor; he continued to take photographs, many of which appeared on the cover of the magazine, but still wasn't paid for his efforts. He also wrote and took photographs as a freelancer for Record Changer, Saturday Review, and other publications.

Gottlieb left Down Beat in the late 1940s, and had a long career as a producer of educational filmstrips. In 1979, after his retirement, he published The Golden Age of Jazz, a collection of his photos.

According to the Library of Congress, which has acquired all of Gottlieb's 1,700 photographs, his work has appeared on hundreds of album covers and on posters, postcards, calendars, and T-shirts, as well as in the press. The U.S. Postal Service used Gottlieb's images of Holliday, Parker, Mildred Bailey, and Jimmy Rushing for a series of stamps honoring jazz greats.