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Errol Flynn Was Old Hollywood's Golden Boy Who Also Lived A Bawdy Life

Updated September 4, 2020 318.1k views11 items

Known for roles in old Hollywood classics like The Adventures of Robin Hood and Captain Blood, Errol Flynn was one of the most popular film stars of the 1930s and 1940s. However, the debonair star's real life differed from that of his movies as he led a life full of scandals, alcohol, underage romances, and other bad behavior. Flynn was one of many Hollywood legends who took advantage of his fame and got caught up in the Hollywood system, but his stories about his antics go beyond pranks and play, entering into harassing and criminal. 

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  • Flynn Was Expelled from Almost Every School He Attended

    Born in Hobart, Australia, in 1909, Errol Flynn was the son of a successful marine biologist and had access to elite schools because of it.

    When his father began teaching in England, Flynn was enrolled at the Southwest London College, an experience he described  as the "most dismal two years of his life."At school, his rambunctious spirit didn't make Flynn a good student, and he was caught up in trouble wherever he went. In his autobiography, Flynn claimed one of the teachers at Southwest London College made sexual advances toward him, and that when he was expelled, it was because he had skipped too many classes, pranked the headmasters too much, and spent too many nights off campus.

    He was sent back to Australia, where he attended grammar school in Sydney. He was supposedly expelled after he got into a fight with another boy over a girl. There were also rumors that he had been caught sleeping with the laundress' daughter, and that he was a bully who stole money from other students. After this expulsion, he had to find his own schools in Australia: his father taught in England and his mother lived in France with her sister.

  • Flynn Bounced Around From Job To Job And Slept With Many Women

    Flynn's education didn't pan out, so he began to work. He worked odd jobs and got engaged to a woman named Naomi for a time, but it was as short-lived romance. 

    In 1927, Flynn took up boxing and gained some local notoriety. His next move was to chase gold in New Guinea. He arrived in New Guinea in October 1927.  He spent most of his time swimming and playing sports, on one occasion taking up with a woman named Maura. Maura was married and, after her husband found out, he beat them both. 

  • Once He Got To England, His Acting Career Took Off

    After moderate financial success in New Guinea, a brief return trip to Australia, and trips from the South China Sea to the Mediterranean, Flynn arrived in England in 1933. Flynn had done his first bit of successful film work during this time, playing a mutineer in In the Wake of the Bounty. This allegedly inspired him to pursue acting.

    In England, Flynn looked for work but was unable to find a job until the Northampton Repertory Company hired him in 1933. He managed to get some acting work in a few British films and signed a contract with Warner Brothers in Hollywood. His big break came when lead actor Robert Donat backed out of the film Captain Blood in 1935 and Flynn took his place. His physique and on-screen appeal led to him being typecast into more roles where he played a swashbuckling adventurer, including The Adventures of Robin Hood in 1938.

  • The Phrase 'In Like Flynn' Describes His Personal Escapades

    Onscreen, Flynn was dashing, charismatic, and appealing, and offscreen it was very much the same. Flynn romanced women at every stop along the way of his rise to stardom. He earned a reputation in Hollywood for excessive drinking and womanizing. His sexual pursuits were successful, however, and maybe it's not a coincidence the phrase "in like Flynn" indicates quick and easy success.