Errol Flynn, the swashbuckling star of Hollywood’s Golden Age, lived a life as thrilling as the films he starred in. 

Real-Life Swashbuckler

Known for playing dashing heroes in films like Captain Bloodand The Adventures of Robin Hood, Errol Flynn wasn’t just pretending to be an adventurer—he lived the part! Before his acting career took off, Flynn sailed the seas, tried his hand at pearl diving, and even looked for gold in New Guinea. His real-life exploits were almost as daring as his on-screen sword fights.

The King of Scandals

Flynn’s off-screen life was filled with controversy. He became famous for his wild partying, affairs, and brushes with the law. His reputation as a Hollywood bad boy was so notorious that the phrase "In like Flynn" was coined to describe his supposed ease in seducing women and getting into trouble. He was even tried (and acquitted) on charges of statutory rape in a highly publicized case, adding to his scandalous reputation.

He Owned a Private Island

Flynn’s thirst for adventure extended to his love for the ocean. He purchased a private island in Jamaica, where he spent much of his time when not in Hollywood. Flynn loved sailing, and his island became the perfect retreat from his chaotic life in the spotlight. He once described Jamaica as "more to me than any woman I have ever known."

Failed at Farming

Before becoming a movie star, Flynn tried his hand at farming—but it didn’t go well. After inheriting a family farm in Tasmania, Australia, Flynn quickly proved to be a terrible farmer. He spent most of his time chasing adventure, leaving the farm neglected. His misadventures in farming ended when he decided to give up that life and head to Hollywood.

War Hero or Exaggerator

Flynn always had a larger-than-life persona, and this extended to his claims of being a war hero. During World War II, he repeatedly tried to enlist but was turned down due to health issues, including heart problems and tuberculosis. Despite not serving, he often exaggerated stories about his supposed war exploits, further fueling his reputation as a daring adventurer.

Died Broke

Despite his fame and fortune, Flynn’s reckless lifestyle eventually caught up with him. He died broke at the age of 50 in 1959, his fortune squandered on lavish parties, yachts, and legal fees. His financial mismanagement was so severe that his assets barely covered the funeral expenses. However, his larger-than-life legacy continues to live on, immortalized by his iconic roles.

He Was Australian

Many fans are surprised to learn that the swashbuckling star wasn’t born in Hollywood—he was actually born in Tasmania, Australia. Flynn’s accent was well-masked by his charm and wit, helping him seamlessly fit into the roles of romantic European and American heroes. Despite his Australian roots, he spent most of his life in the U.S. and Europe.

Wild Pets

Flynn wasn’t just a lover of wild parties—he also loved wild animals. He famously kept a collection of exotic pets, including monkeys, parrots, and even a kangaroo! His homes were known for being lively, chaotic places where animals roamed freely, adding to his off-screen persona as a lover of adventure and unpredictability.

A Writer at Heart

Flynn was more than just an actor—he was also an aspiring writer. He wrote several books, including his autobiographical memoir, "My Wicked, Wicked Ways", which was published shortly after his death. The book revealed Flynn’s wild lifestyle, candidly discussing his love affairs, brushes with the law, and battles with alcoholism. He also penned novels and screenplays, though none achieved the same level of fame as his acting career.

Health Problems from a Young Age

Though Flynn was known for his robust, athletic image on screen, he struggled with serious health problems throughout his life. He suffered from recurring bouts of malaria, tuberculosis, and heart issues, which took a toll on his body. By the time he reached his 40s, Flynn looked much older than his years, and his health had seriously deteriorated due to a combination of illness and his excessive lifestyle.

Lifelong Friendship with David Niven: 

Flynn’s closest friend in Hollywood was fellow actor David Niven. The two shared many wild adventures together, both on and off the screen. Niven once said that living with Flynn was like being on a permanent roller coaster—an exhilarating but dangerous ride! Their friendship became legendary in Hollywood, with both actors’ escapades often filling the gossip columns.