Errol was taken to Sydney, New South Wales, as a child where he attended Sydney Church of England Grammar School (Shore School), from which he was expelled for fighting and, allegedly, having sex with a school laundress . He was also expelled from the next schools he attended. At 20 he moved to New Guinea, where he bought a tobacco plantation, a business which failed. A copper mining venture in the hills near the Laloki Valley behind the present national capital, Port Moresby, also failed.
In the early 1930s, Flynn left for Britain and, in 1933, got an acting job with Northampton Repertory Company, where he worked for seven months. According to Gerry Connelly's book Errol Flynn in Northampton, he also performed at the 1934 Malvern Festival as well as in Glasgow and London's West End.
In 1933, he starred in the Australian film In the Wake of the Bounty directed by Charles Chauvel, and in 1934 appeared in Murder at Monte Carlo, produced at the Warner Bros. Teddington Studios, UK.. This latter film is now considered a lost film. During the filming of Murder at Monte Carlo, Flynn was discovered by a Warner Brothers executive, signed to a contract, and shipped to America as a contract actor. In 1942, Flynn became a naturalized citizen of the United States.
Flynn became an overnight sensation with his first starring role in Captain Blood (1935). He became typecast as a swashbuckler and made a host of such films, including The Adventures of Robin Hood (1938), The Dawn Patrol (1938) with his close friend David Niven, Dodge City (1939), The Sea Hawk (1940), and Adventures of Don Juan (1948).
Flynn played opposite Olivia de Havilland in eight films, including Captain Blood, The Charge of the Light Brigade (1936), The Adventures of Robin Hood, Dodge City, Santa Fe Trail (1940), and They Died with Their Boots On (1941). While Flynn acknowledged his attraction to her, film historian Rudy Behlmer's assertions that they were romantically involved during the filming of Robin Hood (see the Special Edition of Robin Hood on DVD, 2003), have been disputed by de Havilland. Their relationship was, she said in an interview for Turner Classic Movies, platonic, mostly because Flynn was already married to Lili Damita. The Adventures of Robin Hood was Flynn's first in Technicolor.
During the shooting of The Private Lives of Elizabeth and Essex (1939), Flynn and co-star Bette Davis had some legendary off-screen fights, with Davis striking him harder than necessary while filming a scene. Their relationship was always strained, but Warner Brothers teamed them up twice. Their off-screen relationship was later reconciled. A contract was even presented to lend them out as Rhett Butler and Vivien Leigh in Gone with the Wind but the teaming failed to materialize.
Flynn was a member of Hollywood's cricket club along with David Niven. His suave, debonair, and devil-may-care attitude towards both ladies and life has been immortalized in the English language by author Benjamin S. Johnson as "Errolesque" in his treatise on the subject, An Errolesque Philosophy on Life.
After America entered World War II Flynn was often criticised for his failure to enlist while continuing to play war heroes in films. Flynn in fact had actually attempted to join every arm of the services but been rejected for health reasons. The studios' failure to counter the criticism was due to a desire to hide the state of Flynn's health. Not only did Flynn have an enlarged heart, which had already resulted in several heart attacks, but he also suffered from tuberculosis, a painful back (for which he self-medicated with morphine and later, with heroin), and suffered from recurrent bouts of malaria which he had contracted in New Guinea.
By the 1950s, Flynn had become a parody of himself. Heavy alcohol and drug abuse left him prematurely aged and bloated, but he won acclaim as a drunken ne'er-do-well in The Sun Also Rises (1957), and as his idol John Barrymore in Too Much Too Soon (1958). His autobiography, My Wicked, Wicked Ways, was published just months after his death and contains humorous anecdotes about Hollywood. Flynn wanted to call the book In Like Me, but the publisher refused. In 1984, CBS produced a television mini-series based on Flynn's autobiography, starring Duncan Regehr as Flynn.
Flynn was famous for his drinking, womanizing, and brawling. His freewheeling, hedonistic lifestyle caught up with him in November 1942 when two underage chorus girls, Betty Hansen and Peggy Satterlee, accused him of statutory rape. A group was organized to support Flynn, named the American Boys' Club for the Defence of Errol Flynn (ABCDEF); its members included William F. Buckley, Jr.. The trial took place in January and February, 1943, and Flynn was cleared of the charges. The incident, however, served to increase his reputation as a ladies' man, which led to the popular belief that the term "in like Flynn" was based on Flynn's romantic exploits, but that may not be the case.
In the late 1950s, Flynn met the 15-year-old Beverly Aadland at the Hollywood Professional School, whom he courted during his last few years, and cast in his final film, Cuban Rebel Girls (1959). According to Aadland, he planned to marry her and move to their new house in Jamaica, but during a trip together to Vancouver, British Columbia, he died of a heart attack.
His only son, Sean, an actor and later a noted war correspondent, disappeared in Cambodia in 1970 during the Vietnam War while working as a freelance photojournalist for Time magazine; he was presumed killed in mid-1971 by the Khmer Rouge. Although officially declared dead in 1984, his remains have never been discovered. Sean's life was recounted in Inherited Risk by Jeffrey Meyers (Simon & Schuster) and he is also mentioned on page 194 in the Colleagues section of "Dispatches" by Michael Herr. Flynn's daughter Rory, has one son, Sean Rio Flynn, named after her half-brother. Young Flynn is an actor. Rory Flynn has written a book about her father entitled The Baron of Mulholland.
Legend surrounds Errol Flynn's death. According to Vancouver history, Flynn flew with Aadland to Vancouver on October 9, 1959, to sell his yacht Zaca to millionaire George Caldough. On October 14, Caldough was driving Flynn to the airport when Flynn felt ill. He was taken to the apartment of Caldough's friend, Dr. Grant Gould, uncle of noted pianist Glenn Gould. A party ensued, with Flynn regaling guests with stories and impressions. Feeling ill again, he announced "I shall return" and retired to a bedroom to rest. A half hour later, Aadland checked in on him and discovered him unconscious, due to his having suffered a massive heart attack. According to the Vancouver Sun on December 16, 2006, "When Errol Flynn came to town in 1959 for a week-long binge that ended with him dying in a West End apartment, his local friends propped him up at the Hotel Georgia lounge so that everyone would see him."
He is interred in Forest Lawn Memorial Park Cemetery, in Glendale, California. He shares coffin space with six bottles of whiskey, a parting gift from his drinking buddies. Both his parents survived him.
Subsequent biographies — notably Tony Thomas' Errol Flynn: The Spy Who Never Was (Citadel, 1990) and Buster Wiles' My Days With Errol Flynn: The Autobiography of a Stuntman (Roundtable, 1988) — have denounced Higham's claims as pure fabrication. Flynn's political leanings actually appear to have been leftist - he was a supporter of the Spanish Republic in the Spanish Civil War and of the Cuban Revolution, even narrating a documentary titled Cuban Story shortly before his death.
In his biography of Flynn, Satan's Angel (2000), David Bret states that on the set of Captain Blood (1935), during the bare-chested flogging scene, Flynn loudly protested when director Michael Curtiz, fearful of incurring the wrath of the Hays Office, turned up on the set with a razor to cut off Ross Alexander's exhuberant armpits which "turned him on like twin fannies". "Errol grabbed this, and threatened to slit the director's throat should he remove so much as one hair from Alexander's 'magnificent oxters', so the scene was left uncut, and received few complaints."
Flynn wrote the following books: