Errol Flynn: The Scandalous Truth Behind Hollywood’s Most Daring Star

Born in Tasmania in 1909, Errol Flynn rose to fame during Hollywood’s Golden Age to become one of the most recognizable film stars in the world. With his effortless charm, striking good looks and flair for swashbuckling roles, he became one of Warner Bros.’ most bankable leading men.

But behind the dazzling smile and on-screen heroics was a complicated figure. Beneath the fame lay a darker reality marked by excess, scandal and a relentless appetite for pleasure.

A Pattern of Trouble From the Start

Flynn school picture
Evening Standard / Getty Images
Evening Standard / Getty Images

Errol Flynn was born in Tasmania on June 20, 1909, and after spending some time in Papua New Guinea, returned to Australia to attend a fancy grammar school. That didn't last all that long, as he was expelled.

This was his first real encounter with public controversy, something he'd become very familiar with in his professional life. While some stories claim he was expelled for stealing, Flynn boasted that he was kicked out for having intimate relations with a school laundress.

The true story? No one knows for sure.

ADVERTISEMENT

It Didn't Take Much for Errol Flynn to Blow Up in Popularity

ADVERTISEMENT
Flynn in Captain Blood
Warner Bros. / MovieStillsDB
Warner Bros. / MovieStillsDB
ADVERTISEMENT

After having a few small parts in films, Flynn found himself being considered for a big-time role in the 1935 swashbuckler film, Captain Blood. While he was essentially unknown at the time, his initial screen test proved to be enough for the studio and the part was his.

ADVERTISEMENT

Warner Bros.' judgment turned out to be right. The movie was a smashing success, turning Flynn into a major star in the blink of an eye.

ADVERTISEMENT

Playing Robin Hood Defined His Career

ADVERTISEMENT
ADVERTISEMENT
the-adventures-of-robin-hood_Ja142k
Warner Bros. / MovieStillsDB
Warner Bros. / MovieStillsDB
ADVERTISEMENT

At 28, Flynn starred in the 1938 film The Adventures of Robin Hood, which turned out to be the sixth highest-grossing movie of the year and Warner Bros.' first large-budget color feature using the three-strip Technicolor process. Costing a whopping $2.47 million, it was the most expensive film the studio had produced at that time.

ADVERTISEMENT

The Adventures of Robin Hood was hailed by critics and is still held in high regard today. It also won three Academy Awards.

ADVERTISEMENT

Prevented From Serving in World War II

ADVERTISEMENT
ADVERTISEMENT
Errol Flynn in front of blue background
Silver Screen Collection / Getty Images
Silver Screen Collection / Getty Images
ADVERTISEMENT

Even though he was a Hollywood star, Flynn answered the call when the US became involved in World War II. However, while he tried to enlist in the military, he was rejected due to numerous health concerns.

ADVERTISEMENT

Warner Bros. tried to cover up that he had been rejected, as it didn't look good for their biggest action star to have health problems. This resulted in rumors spreading that Flynn had dodged the draft. Later in his life, he proclaimed that his only regret was not serving in the conflict.

ADVERTISEMENT

The Spy Rumors That Followed Flynn

ADVERTISEMENT
ADVERTISEMENT
Flynn in a tuxedo
Sasha / Getty Images
Sasha / Getty Images
ADVERTISEMENT

In 1980, one of Flynn's biographers falsely published in his book, Errol Flynn: The Untold Story, that the actor had worked as a German spy before and during the Second World War.

ADVERTISEMENT

He claimed Flynn had arranged for the movie Dive Bomber to be filmed on location at the San Diego Naval Base, in order to provide the Japanese information about US warships and defense information. Highman also penned that Flynn was experimental and had numerous affairs with other men.

It was only later that the author admitted he had no evidence to back up his claims.

ADVERTISEMENT

He Was a Peeping Tom

ADVERTISEMENT
ADVERTISEMENT
Errol Flynn at home
John Kobal Foundation / Getty Images
John Kobal Foundation / Getty Images
ADVERTISEMENT

In 1941, Flynn bought an 11-acre property on Mulholland Drive where he built a two-story colonial-style ranch house that he dubbed as "Mulholland Farm," and, more privately, the "playhouse."

ADVERTISEMENT

Inside of the house, Flynn had secret passageways he had fitted with peepholes and two-way mirrors, so he could spy on girls as they changed or were in the bathroom. On top of that, he installed microphones, so he and his friends could listen to the women discussing the men.

ADVERTISEMENT

Errol Flynn Found Himself in Deep Legal Trouble

ADVERTISEMENT
ADVERTISEMENT
Errol Flynn on trial
Bettmann / Getty Images
Bettmann / Getty Images
ADVERTISEMENT

In 1942, two 17-year-old girls accused Flynn of inappropriate behavior at the Bel Air home of Frederick McEvoy and on Flynn's yacht. The press had a field day with the scandal, although many members of the public sided with Flynn against the accusations.

ADVERTISEMENT

The trial occurred in February 1943, with Flynn's lawyer putting the girl's character into question. He also accused them of working together to avoid prosecution themselves. Although Flynn was acquitted, the scandal permanently damaged his image.

ADVERTISEMENT

He Was Always on the Prowl

ADVERTISEMENT
ADVERTISEMENT
Flynn and Nora
Bettmann / Getty Images
Bettmann / Getty Images
ADVERTISEMENT

While on trial in 1942, Errol Flynn's attention turned to something else other than possibly being found guilty. That something - or someone - was Nora Eddington, a 19-year-old working at the cigarette cart at the courthouse during the trial.

ADVERTISEMENT

It wasn't long before the two struck up a romantic relationship, and they were married in 1943. The couple had two daughters although they divorced in 1949.

ADVERTISEMENT

Flynn Became Involved in Yet Another Scandal

ADVERTISEMENT
ADVERTISEMENT
Aadland and Flynn
Bettmann / Getty Images
Bettmann / Getty Images
ADVERTISEMENT

In the last two years of his life, Errol Flynn was involved with yet another scandal when he traveled with a 15-year-old secretary. The underage girl was also his mistress, and the relationship had been arranged by her mother, who'd later proudly write a book about it.

ADVERTISEMENT

In an interview, the teenager claimed that, although Flynn initially forced himself on her, she grew to love him and wished they'd had more time together.

ADVERTISEMENT

He Was No Stranger to the Bottle

ADVERTISEMENT
ADVERTISEMENT
Flynn sitting down
John Kobal Foundation / Getty Images
John Kobal Foundation / Getty Images
ADVERTISEMENT

Throughout his life, Errol Flynn was known to alcohol abuse. At one point, he even managed to get thrown out of a party hosted by William Randolph Hearst at Hearst's Castle. On top of that, he once got into a physical altercation with director John Huston for his behavior, resulting in him getting knocked out in one punch.

ADVERTISEMENT

As a result of his drinking, Errol was banned on most sets from touching alcohol, so he was known to inject his oranges with vodka to get his fix. Following his death, it was concluded his liver was in such bad shape that he would have died within a year anyway.

ADVERTISEMENT

When Drinking Wasn't Enough

ADVERTISEMENT
ADVERTISEMENT
Flynn on a boat
Hulton Archive / Getty Images
Hulton Archive / Getty Images
ADVERTISEMENT

While it was well known Flynn was a raging alcoholic, that wasn't the only substance he was known to ingest. Over the years, he began experimenting with a series of other substances.

ADVERTISEMENT

According to his second wife, Flynn was determined to experience as much as he could, leading him to try opium in the 1940s. Unfortunately, it became another addiction that he would struggle with for the rest of his life.

ADVERTISEMENT

Flynn Had Issues With Director Michael Curtis

ADVERTISEMENT
ADVERTISEMENT
On the set of Robin Hood
Bettmann / Getty Images
Bettmann / Getty Images
ADVERTISEMENT

Despite working together on several films, Flynn and director Michael Curtiz weren't friendly. It's assumed one of the primary sources of their animosity was Flynn's first wife, Lili Damita, who'd initially been married to Curtiz.

ADVERTISEMENT

On several occasions, the two became involved in physical altercations. The first was when Flynn was struck by a sword without a protective tip Curtiz had instructed to be removed, causing Flynn to grab him by the throat. The second happened after 25 of 125 horses died after Curtiz set up a line of tripwires while filming a pack of charging horses for a more dramatic scene.

ADVERTISEMENT

Stanley Kubrick and Ernest Hemingway

ADVERTISEMENT
ADVERTISEMENT
Errol Flynn
Bettmann / Getty Images
Bettmann / Getty Images
ADVERTISEMENT

In the 1950s, Flynn met up with director Stanley Kubrick to discuss the possibility of acting in his adaptation of Vladimir Nabokov's controversial novel, Lolita, about a man obsessed with a 12-year-old girl. However, nothing ever happened, possibly because of Flynn's muddy past regarding underage women.

ADVERTISEMENT

In the last few years of his life, Flynn went from playing the leading man to alcoholic supporting roles. One of these most notorious was an adaptation of Ernest Hemingway's The Sun Also Rises, with the actor's performance being the only part of the film Hemingway enjoyed.

ADVERTISEMENT

He Had a Connection to Cuba

ADVERTISEMENT
ADVERTISEMENT
Errol Flynn manning the helm of 'Zaca'
Bettmann / Getty Images
Bettmann / Getty Images
ADVERTISEMENT

In 1958, Flynn went to Cuba to self-produce Cuban Rebel Girls. There, he met Fidel Castro, as he was a supporter of the Cuban Revolution.

ADVERTISEMENT

The actor went on to write a number of newspaper and magazine articles for the New York Journal American and other publications, documenting his time with the revolutionary. He was also the only journalist with Castro the night he learned of his victory in the revolution.

ADVERTISEMENT

A Cruel and Sick Joke

ADVERTISEMENT
ADVERTISEMENT
Errol in tuxedo
Silver Screen Collection / Getty Images
Silver Screen Collection / Getty Images
ADVERTISEMENT

Flynn's friend, director Raoul Walsh, claims to have played a prank on the actor the day after the death of John Barrymore. Supposedly, Walsh bribed the mortician to release the body to him. He then set it up on a chair holding a drink inside of Flynn's home.

ADVERTISEMENT

In his autobiography, My Wicked, Wicked Ways, Flynn noted, "As I opened the door, I stared into the face of Barrymore. His eyes were closed. He looked puffed, white, bloodless. They hadn't embalmed him yet. I let out a delirious scream. My heart pounded. I couldn’t sleep for the rest of the night."

ADVERTISEMENT

He Was Quite the Womanizer

ADVERTISEMENT
ADVERTISEMENT
Flynn on fishing trip
Bettmann / Getty Images
Bettmann/Getty Images
ADVERTISEMENT

Even before becoming one of the most famous actors in the world, Flynn was known for his love of women, which only increased the more popular he became. According to his close friend, David Niven, "Flynn's attitude to women perhaps began with his strained relationship with his mother, Marielle. From age five, Flynn witnessed her affairs with other men, and she abused him regularly."

ADVERTISEMENT

Throughout his life, Flynn was married three times and had countless affairs, with some of the most notable women, including Joan Bennett, Ann Sheridan, Ida Lupino and numerous others.

ADVERTISEMENT

A Relationship That Was Surprisingly Never Intimate

ADVERTISEMENT
ADVERTISEMENT
Flyn and Havilland in Captain Blood
Silver Screen Collection / Getty Images
Silver Screen Collection / Getty Images
ADVERTISEMENT

Over the course of his career, Errol Flynn made a total of nine films with Olivia de Havilland, more often than not as a romantic couple. Of course, rumors began circulating that the two were romantically involved off-screen.

ADVERTISEMENT

Although this wouldn't be a first for Flynn, de Havilland was firm in her response that there was no such relationship going on. She even admitted that she felt a romantic attraction to Flynn, but never acted on it out of respect for his marriage.

ADVERTISEMENT

Errol Flynn Wasn't Loved By All Women

ADVERTISEMENT
ADVERTISEMENT
Flynn and Davis
Bettmann / Getty Images
Bettmann / Getty Images
ADVERTISEMENT

Although Flynn was a renowned ladies man for most of his life, there was one actress who saw right through him: Bette Davis, with whom he'd worked on numerous films during the height of his career. Davis couldn't stand Flynn, with him accusing her of slapping him overly hard in scenes just because she didn't like him.

ADVERTISEMENT

Davis attributed her hatred to being forced to share a screen with someone she thought could only act in swashbuckler films.

ADVERTISEMENT

His Son Was Lost.. And Never Found

ADVERTISEMENT
ADVERTISEMENT
Sean Flynn at a party
Earl Leaf / Michael Ochs Archives / Getty Images
Earl Leaf / Michael Ochs Archives / Getty Images
ADVERTISEMENT

Errol Flynn only had one son, Sean, who also became an actor. However, he eventually put his career on hold to follow his true passion: journalism.

ADVERTISEMENT

During the Vietnam War, Sean traveled to southeast Asia as a war correspondent for Time. Tragically, he disappeared while in Cambodia in 1970. Fourteen years later, he was declared as dead, although his body was never recovered. Luckily for Flynn, he wasn't alive to suffer through this kind of loss.

ADVERTISEMENT

A Change in Titles

ADVERTISEMENT
ADVERTISEMENT
Flynn in a white t shirt
Hulton Archive / Getty Images
Hulton Archive / Getty Images
ADVERTISEMENT

Errol Flynn was no stranger to embellishing stories or boasting about his accomplishments and exploits, so it's no surprise that, when he wrote his autobiography, he wanted to title it In Like Me, a play on the saying "in like Flynn," which referred to his ability to seduce just about any woman that he set his eyes on.

ADVERTISEMENT

However, Flynn's publicist suggested that he go with something a little less aggressive and the autobiography was titled My Wicked, Wicked Ways.