His best known work is arguably a collection of 2,500 photographs, some nude or semi-nude, taken of Marilyn Monroe over a three day period, six weeks before her death. As they were the last posed photographs taken of Monroe, the portfolio has come to be known as "The Last Sitting". The photographs were taken for Vogue, who published several of them following Monroe's death. A book containing these photographs, including copies of proofs over which Monroe had written comments, or crossed out with lipstick, was published in 1992 with the title Marilyn Monroe: The Complete Last Sitting.
He also directed Jazz on a Summer's Day, a 1959 documentary film set at the 1958 Newport Jazz Festival. It was filmed and directed by noted commercial and fashion photographer Bert Stern. In 1999 the film was deemed "culturally significant" by the United States Library of Congress and selected for preservation in the National Film Registry.
Stern worked as a photographer on the film Lolita (1962) and was responsible for the publicity photographs of its star Sue Lyon. He has photographed celebrities such as Audrey Hepburn, Elizabeth Taylor, Madonna, Kylie Minogue and Drew Barrymore in addition to his work for advertising and travel publications.