The Diary of Anne Frank
The most poignant “what if” is the 1959 film, The Diary of Anne Frank. Not only was Hepburn the top choice of director George Stevens, but she was also the personal pick of Anne's father, Otto Frank. The connection was deeply personal: Hepburn was born
the same year as Anne and spent her adolescence in the Nazi-occupied Netherlands, living just miles away. She suffered from malnutrition during the Dutch famine and witnessed the horrors of the occupation, including the public execution of her own uncle. Ultimately, Hepburn declined the role, finding it too emotionally devastating to relive the trauma. She was reportedly so destroyed by reading the diary, which she called Anne her "soul sister," that she couldn't bear to portray the experience on screen. While Millie Perkins was eventually cast as Anne, it was Shelley Winters who won the Best Supporting Actress Oscar for her role as Mrs. Van Daan, an award she later donated to the Anne Frank Museum.
West Side Story
Imagine Audrey Hepburn as Maria in the gritty, vibrant world of West Side Story. The producers of the 1961 musical wanted her for the lead, but she turned it down for a very personal reason: she was pregnant and, having suffered previous miscarriages, was unwilling to take on the physically demanding role. The part went to Natalie Wood, and the film became a phenomenon, winning 10 Academy Awards, including Best Picture. Ironically, both Wood's and Hepburn's singing voices were dubbed in their most famous musicals—Marni Nixon sang for both Wood in West Side Story and Hepburn in My Fair Lady. Another role in the film, Anita, earned Rita Moreno an Oscar, adding another Academy Award winner to the list of films Hepburn passed on.
Cleopatra
Before Elizabeth Taylor secured her then-record-breaking $1 million contract to play the Egyptian queen, Audrey Hepburn was one of the directors' first choices for the epic 1963 film Cleopatra. At the time, Hepburn reportedly declined by saying she was trying to get pregnant. The role instead went to Taylor, and the production became one of the most notoriously expensive and dramatic in history. It was on the set of Cleopatra that Taylor and Richard Burton began their tempestuous, world-famous romance. While Hepburn’s career was defined by elegance and restraint, it’s fascinating to picture her at the center of such a lavish and chaotic Hollywood blockbuster.
The Exorcist
In perhaps the most startling what-if, Hepburn was offered the lead role of Chris MacNeil, the tormented mother in the terrifying 1973 horror classic, The Exorcist. She was reportedly interested in the script but had one non-negotiable condition: the film had to be shot in Rome, where she was living with her family. The producers, committed to a U.S. production, declined her request. The role ultimately went to Ellen Burstyn, who received an Academy Award nomination for her powerful performance. It’s hard to imagine the graceful icon in such a visceral, terrifying film, which makes her connection to it all the more intriguing.
Gigi
Audrey Hepburn's career first took off on Broadway when she starred in the 1951 play Gigi. When it came time to make the lush 1958 musical film version, she was the natural choice to reprise her role. However, after a long and exhausting run on stage, she declined the film. The part of the Parisian girl-in-training went to another enchanting actress, Leslie Caron. The film was a massive success, sweeping the Oscars with nine wins, a record at the time. While Hepburn had already won her own Oscar for Roman Holiday, passing on Gigi meant stepping away from a role she had originated and helped make famous.












