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Errol Flynn – Hollywood’s Greatest Swashbuckler Led a Much Darker Private Life

Katie Vernon

‘I like my whiskey old, and my women young’ said Errol Flynn, the romantic swashbuckler from the Hollywood movies. He was one of the most famous actors in the 1930s and 1940s whose unmatched charm made him famous but his deviant personality brought for his downfall.

Flynn was born in Hobart, Tasmania in 1909 and was problematic and eccentric throughout his childhood. After being expelled from school for theft, he spent some time in Papua, New Guinea and Sydney, Australia before moving to London. However, unable to settle into British society, he soon returned home.

Errol Flynn
Errol Flynn

He tried going to school again, at the Sydney Church of England Grammar School but was again expelled, allegedly for having sex with the school laundress. After that, he worked as a clerk but soon lost the job for stealing petty cash.

Being handsome and charismatic brought Flynn to the world of cinema. In 1933, he appeared in a low budget Australian movie In the Wake of the Bounty as an amateur actor in the lead role as Christian Fletcher. However, it was obvious to everyone, mostly to Flynn himself that he lacked a lot of knowledge and acting skills.

Errol Flynn at the age of nine, as a page boy in the Queen Carnival pageant held in Burnie, Tasmania. On his right is Enid Lyons, who would later become the first woman elected to the Australian House of Representatives.
Errol Flynn at the age of nine, as a page boy in the Queen Carnival pageant held in Burnie, Tasmania. On his right is Enid Lyons, who would later become the first woman elected to the Australian House of Representatives.

Determined to succeed, Errol sailed back to England where he trained at the Northampton Repertory Company for seven months. Unsurprisingly, he was dismissed after a fight with a female stage manager that involved her falling down some stairs.

Errol Flynn at South West London College aged 14 (1923)
Errol Flynn at South West London College aged 14 (1923)

Regardless of his behavior, Flynn’s irresistible charisma won him the lead role in Murderer at Monte Carlo (now lost) and subsequently a contract with Warner Brothers. So Flynn left Europe and flew to America. In Hollywood, he was an immediate sensation, and his career began to flourish.

Flynn and first wife, Lili Damita, at Los Angeles airport in 1941.
Flynn and first wife, Lili Damita, at Los Angeles airport in 1941.

In 1935, he started in Captain Blood and The Sea Hawk. Bringing back popularity to the adventure movies, Flynn was regularly cast as a dashing adventurer, famous for his fast-paced and well-choreographed sword fights. Some consider Flynn to be the greatest swashbuckler of all.

Flynn in That Forsyte Woman (1949).
Flynn in That Forsyte Woman (1949).

He and Olivia de Havilland appeared together in nine movies becoming one of Hollywood’s most popular romantic on screen pairings. Although both of them admitted that there was chemistry between them backstage, nothing ever happened because of Flynn’s marriage to the French actress Lili Damita. They married in 1935 but divorced in 1942.

Flynn was known for his heavy drinking, womanizing, and chain smoking. He was often involved in scandals which were damaging to his public image.

Errol Flynn with Olivia de Havilland in Santa Fe Trail (1940).
Errol Flynn with Olivia de Havilland in Santa Fe Trail (1940).

Great Hollywood legends quotes

In 1942, Flynn became an American citizen and applied to join the armed services but was found unfit due to several health problems.

He suffered from an enlarged heart (with probably at least one heart attack at the time); recurrent malaria which he contracted during his time in New Guinea; chronic back pain for which he regularly took morphine and later heroin; lingering chronic tuberculosis; and six separate STDs.

Errol Flynn with Olivia de Havilland in The Adventures of Robin Hood (1938).
Errol Flynn with Olivia de Havilland in The Adventures of Robin Hood (1938).

At around the same time, new genres such as film noir and urban realism changed the public’s taste. Flynn, mastering the English-based epics, was unable to make the transition and the quality of his acting dropped. Hollywood didn’t worry — there were countless other talented actors waiting to get on screen, and Flynn was released from his contracts

By 41, Errol’s acting career has ended. The fact that he was no longer on the set might have made his collaborators relieved as there were numerous reports about his disruptive behavior on stage.

Errol Flynn and Bette Davis.
Errol Flynn and Bette Davis.

Vanity Fair reports that in 1943, Errol Flynn was accused of statutory rape by two underage girls. Even though he was acquitted, his public image was ruined forever. On top of everything, he secretly married in Mexico, to 19-year-old Nora Eddington who worked in the courtroom and whom he met during his trial. They had two children before divorcing in 1949. This period of Flynn’s life has been dramatized in the film The Last of Robin Hood starring Kevin Kline as Flynn.

Errol Flynn’s coffin on a Union Station railway platform in Los Angeles.
Errol Flynn’s coffin on a Union Station railway platform in Los Angeles.

Flynn continued drinking, smoking, and womanizing, ruining his health and what was left of his reputation. His last known work was a narrated short film about Fidel Castro.

In the 1950s, he suffered from liver damage and hepatitis, with his body finally giving up in 1959 when Errol Flynn died of a heart attack.

Read another story from us: The Golden Hollywood Marriage that Began in Secret and Ended in Mental Illness

But nothing can beat Flynn’s charisma. Nobody resisted his charm, neither young women, nor Hollywood. Decades after his death, Errol Flynn’s life remains a subject of many biographies and films.

Katie Vernon

Katie Vernon is one of the authors writing for The Vintage News