Legends of Hollywood: The Life of Errol Flynn

"The public has always expected me to be a playboy, and a decent chap never lets his public down." - Errol Flynn

Hollywood has never lacked leading men who could captivate viewers with dramatic performances that depict them as suave romantics or dashing heroes, especially during the Golden Age of Hollywood when stars like Humphrey Bogart, Clark Gable, and Cary Grant graced screens. But in 1940, the 4th most popular star in the U.S. was a foreign actor from Australia, and unlike other movie stars, he was more notorious for his pursuits off the screen than on it. In an era long before social media and TMZ, Errol Flynn represented the epitome of a swashbuckling playboy, with enough mystery and intrigue surrounding him and his background to fascinate even those who didn't see his movies. An article in Time magazine got to the heart of the matter in 1938 when it noted, "Of all the heroes of Hollywood, Errol Flynn has by long odds the greatest amount of non-phony glamor. His life has been as adventurous as any of the swashbuckling characters he has portrayed. At 18 he was a member of the English Olympic boxing team. At 19 he was master of an island trading schooner in the South Seas. He has chased head-hunters in New Guinea and "recruited" blacks for British miners. Once he made $5,000 mining gold, got drunk and blew it all on a schooner, The Sirocco, which he sailed in the South Seas and wrote a book about (Beam Ends)."

Even Hollywood stars accustomed to mingling with each other were awestruck by Flynn, who was an industry newcomer in 1935 but a huge star in just a few years. When Olivia de Havilland, who would eventually become an Academy Award winner and played Melanie in Gone With the Wind, met Flynn ahead of appearing with him in Captain Blood (1935), she recalled, "And I walked onto the set, and they said, 'Would you please stand next to Mr. Flynn?' and I saw him. Oh my! Oh my! Struck dumb. I knew it was what the French call a coup de foudre. So I took my position next to him...We had never met, and we just stood there next to each other. Oh!" Studio head Jack Warner once offered quite a flattering description as well: "He was all the heroes in one magnificent, sexy, animal package. I just wish we had someone around today half as good as Flynn."

Naturally, when he was at the peak of his powers both on and off the screen, Flynn frequently joked about his lifestyle and traded upon it for popularity, with comments like "I like my whisky old and my women young" and "Women won't let me stay single and I won't let me stay married." Not surprisingly, Flynn was just as fast and loose with his money, to the extent that he once asserted, "Any man who has $10,000 left when he dies is a failure." This led many to assume that far from being content with life, Flynn was actually "tormented" (as de Havilland once put it) or covering up his own insecurities, as actress Ann Sheridan suggested: "He was one of the wild characters of the world, but he also had a strange, quiet side. He camouflaged himself completely. In all the years I knew him, I never knew what really lay underneath, and I doubt if many people did." Flynn himself suggested that was the case, once saying, "I suppose most of us act all our lives. We have a facade, a front. We imagine ourselves to be what we're not, don't we?"

While Flynn's adventurous lifestyle helped cast him in the mold of a 20th century Lord Byron, his quotes and lifestyle also hinted at a self-fulfilling prophecy that would prove destructive, and although he quickly found himself at the top of Hollywood, the same lifestyle that helped make him popular also took its toll on his health, work, and finances.