She was born July 1, 1916 in Tokyo, Japan to Lilian Ruse, a British stage actress and Walter de Havilland, an English professor teaching at the Imperial University in the country. Olivia would have a younger sister born there fifteen months later, Joan de Beauvoir de Havilland (who would later be known as actress, Joan Fontaine). After a few years, Lilian persuaded her husband to take the family back to England for a climate better suited for their daughters whose health was declining. While sailing back, they stopped in San Francisco to get treatment for an ailing Olivia. The couple's marriage was troubled due to de Havilland's infidelities and he would abandon his family and go back to Japan (to later marry their Japanese houskeeper). Ruse remained in the U.S. and took her daughters to live in the town of Saratoga in Santa Clara County, CA.
After divorcing de Havilland, Ruse met George Milan Fontaine, a department store manager in San Jose and they married in 1925. Fontaine would immerse her girls in the arts with lessons in ballet, piano and performance. A teenage de Havilland was drawn to the stage and appeared in a Saratoga Community Theater production of Shakespeare's "A Midsummer Night's Dream" in 1934. Max Reinhardt, a director from Austria, came to California to launch a new production of the same play to premiere at the Hollywood Bowl. One of the director's assistants saw de Havilland perform and offered her an understudy role of Hermia. And in that classic breakthrough opportunity, de Havilland got the chance to go on stage when the assigned performer dropped out a week before production. The director was so impressed by the young actress that he hired her for the touring production. Then Reinhardt was hired by Warner Bros. to direct a filmed version of the play and wanted de Havilland for the movie. Although initially unsure if this was what she wanted to do as a career, she signed a seven-year contract with the studio.
This was the start of de Havilland's long and remarkable movie career and just a few of her memorable performances in film include "Captain Blood" (1935), "The Adventures of Robin Hood" (1938), "The Private Lives of Elizabeth and Essex" (1939), "The Strawberry Blonde" (1941), "The Snake Pit" (1948) and "Hush...Hush, Sweet Charlotte" (1964). She would win her first Academy Award for Best Actress in "To Each His Own" in 1946 and receive a second for her outstanding performance in "The Heiress" in 1949. But the one role that the actress is most closely associated with is Melanie in the big screen adaption of "Gone With The Wind" in 1939. This Civil War drama was immensely popular when first released and would go on to win five Academy Awards including Best Picture. But in recent times, the film has been looked at far more critically, especially problematic is it's depiction and romanticization of slavery.
Following the lead of fellow Warner Bros. contract player, Bette Davis, de Havilland wanted to play more interesting and challenging roles and would turn down parts she felt were beneath her. This would cause her to be occasionally suspended from work. And when her contract was up in 1943, de Havilland discovered that the studio was trying to tack on six more months to her contract due to her work refusals. Feeling this was unfair and illegal, she contacted a lawyer and fought Warner Bros. in court. Two years later, the actress would be victorious and the judgment would become known as the De Havilland Law where a contract could be no longer than seven calendar years.
With de Havilland's sister, Joan Fontaine following her with a Hollywood acting career, this would create long simmering tension and animosity between the siblings. One source of contention was in the year of 1942 when both actresses were nominated for Best Actress Oscars. Fontaine won for her performance in Alfred Hitchcock's "Suspicion" and the sisters would publicly feud and bicker over the years. When Fontaine died in 2013 at the age of 96, de Havilland stated that they had long settled their differences.
In her later years, de Havilland would continue to work on stage, film and television before officially retiring in 1988. She married writer, Marcus Aurelius Goodrich in 1946 and they had a son, Benjamin who died in 1991 from complications of Hodgkin's disease. The couple separated in 1952. De Havilland then married Pierre Galante, another writer who worked for Paris Match, in 1955. She moved to France and they had a daughter, Gisele. She would divorce Galante in 1979 but would remain in Paris for the rest of her life.