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Well, two weeks ago we asked for your pick for favorite Errol Flynn movie, so it’s only fair that this time we turn the spotlight on his frequent leading lady, Olivia de Havilland. It’s even more fitting since this week marks the two-time Academy Award winner’s 109th birthday.
Born in Tokyo in 1916 to British parents, Olivia Mary de Havilland would move as a child to the central California town of Saratoga with her mother and younger sister Joan (more about her to come) after her father left them. While playing Puck in a 1934 local production of A Midsummer Night’s Dream, 18-year-old Olivia came to the attention of director Max Reinhardt. He brought her to Hollywood for his own lavish stage version of the Shakespeare comedy.
When Warner Bros. and Reinhardt adapted Midsummer for the screen in 1935, de Havilland, newly signed to a studio contract, joined an all-star cast that included Joe E. Brown, James Cagney, Dick Powell, and Mickey Rooney. Her actual film debut, though, came earlier that year in the baseball comedy Alibi Ike, opposite Brown. Olivia’s 1935 breakout role was as a Caribbean colonial governor’s niece in the swashbuckler Captain Blood. It was also her first movie with another new Warners star, Australian-born Errol Flynn. Audiences loved the chemistry between the pair, and they went on to make seven more films together.
Over the next five decades de Havilland would star in over 50 motion picture and TV projects. Among her most famous roles were alongside Flynn as Maid Marian in The Adventures of Robin Hood; as Melanie Hamilton Wilkes in Gone with the Wind; her Oscar-winning turns in To Each His Own and The Heiress; twins Ruth and Terry Collins in The Dark Mirror; as a mental hospital patient in The Snake Pit; and as the lady in a cage in…well, Lady in a Cage. Nearly as famous was her long-standing feud with her sister, fellow actress Joan Fontaine. A longtime resident of Paris, de Havilland retired there and lived quietly until her 2020 death at the remarkable age of 104.
Now we’d like to know which of De Havilland’s screen performances is your favorite. Select from the list below, and tell us in the comments if we failed to list your pick.