The 5 faces of Errol Flynn

'I don't know whether I can convey how deep the yearning is of an actor who has been stereotyped, who has the sword and horse wound around him, to prove to himself and to others that he is an actor.'
Errol Flynn

We remember Errol Flynn as Robin Hood, Peter Blood and Don Juan – all of them swashbuckling heroes who are as equally good at fighting as they are at being charming. It was an image that gave Flynn his fame and one that he would return to over and over, but it was also one which trapped him.

‘If a stereotype makes money, keep the stereotype alive. Don’t make a switch. Don’t experiment, don’t pander to an actor’s whim that he might like to do something special, different.’

Flynn wanted to be more than a one-trick-pony and here are 5 films that show how he brought different personas to his films.

Flynn the adventurer: Captain Blood (1935)

Although Robin Hood is probably his most famous role, the swashbuckling pirate, Captain Blood, is where it all started for Flynn in 1935. Originally offered to Robert Donat who had to turn it down due to ill-health and a desire to work more in the UK, it can be viewed as one of those twists of fate that actually turned out for the better.


In real life, pirates can be a pretty rotten bunch, so perhaps that is why although Captain Blood is a pirate film, Flynn doesn’t actually play a pirate at all. His character is actually a doctor who, whilst trying to help an injured man, is falsely accused of treason and shipped to the Caribbean as a slave. There, he is bought by Arabella Bishop (Olivia De Havilland) and sparks fly. It is only after he escapes that he becomes a pirate, although he is a pirate with a moral code and sense of honour. When fellow pirate, Captain Levasseur (played by the fantastic Basil Rathbone), reverts to typical brigand behaviour and captures Arabella, one of the best sword fights on screen ensues.

What makes Flynn so good at the pirate persona is that there is so much of himself in it. The genre allowed the film studios to bypass the Hollywood code and show drinking, fighting, bawdy behaviour and womanising. Flynn was good at all these, although they would eventually lead to his early death at 50. But it was more than that. Flynn was born to play debonair, athletic and dashing heroes, and sword fights were his shop window. He makes a good adventurer because that is exactly what he was – in his memoirs Flynn claimed that he had once been a real-life pirate, and although it may not have been true, somehow it seems possible.


It would not be the last pirate he played: there would also be The Sea Hawke (1941) and Against all Flags (1952). He would also continue to play adventurers, even at the end of his career when his looks were fading and his body was giving up, such as The Master of Ballantrae (1953), his last movie for Warner Brothers. Audiences still believed in him because he was Errol Flynn and he would always be the personification of the handsome, charming rogue.

‘By instinct I’m an adventurer; by choice I’d like to be a writer; by pure, unadulterated luck, I’m an actor.’

Flynn the cowboy: Dodge City (1939)

Flynn was very unsuited to being a cowboy. He was far too clean and sophisticated for a man supposedly living life on horseback. His accent was all wrong and his moustache was what villains had, not heroes.

And yet he made eight westerns during his career beginning with Dodge City in 1939. With him is Olivia De Havilland and Alan Hale, two of his most consistent co-stars, and it is the only one of his westerns where they try to explain away his Tasmanian accent by claiming he was a well-travelled Irish soldier.

In typical Flynn fashion, he begins the film as a man looking to avoid responsibility, wanting a free and easy life, but the death of a boy changes his outlook. The Flynn that now appears is stern, determined and driven. He will not stop until he ends the violence and although he remains charming, he is now a man to be reckoned with. There is no swashbuckling here.

Despite his obvious drawbacks, the film and Flynn were a success, but his subsequent westerns were a slow decline in quality. As with many movies of the era, some of the attitudes towards First Nation tribes, people of colour and slavery are difficult to watch with modern eyes and mar the entertainment factor. But the scene where the young Harry Cole (played by nine-year-old Bobs Watson) is killed after being dragged down the street by wild horses is still one of the most powerful and harrowing depictions of the death of a child in cinema history.

Flynn the historical figure: Gentleman Jim (1942)

Flynn played several historical characters during his career, many of whom had actually existed. In The Private Lives of Elizabeth and Essex he was Robert Devereux; in They Died With Their Boots On he was General Custer; and, of course, Robin Hood.

In Gentle Jim he is the boxer Jim Corbett. Like most biopics, it is highly fictionalised in its telling of the story of the son of an Irish livery driver who works his way from being a bank clerk to a professional boxer. His character is a brash social climber, yet he is charming and stylish and instantly likeable, much like Flynn himself. This is why the film works so well. Flynn is playing Flynn. He is able to make the audience like him and he is a natural contrast to his brutish competitor, John L Sullivan.

But the film also makes sure that he is depicted as a man of honour as when he shows his compassion to his defeated foe at the end of the film. Flynn may be a rogue, but he is a decent one.

Flynn the anti-hero: The Sisters (1938)

The Sisters is one of Flynn’s lesser known movies but it shows a side of him that conflicted with his usual easy-going, heroic character.

The film follows the story of the three Elliott sisters at the turn of the twentieth-century. Flynn plays Frank, a journalist with aspirations of being a novelist, who sweeps Louise, played by Bette Davis, off her feet and away from her fiancé. The marriage runs into trouble due to Frank’s drinking and feelings of being trapped; Flynn is beset by demons, failure and anger which he takes out on his strong and determined wife.


The Sisters was primarily a vehicle for Davis although she had to fight to get her name alongside Flynn’s at top billing. She had already won an Oscar, yet she was only paid $2250 a week compared to his $4500, something that even Flynn acknowledged as ridiculous.

She had been keen to work with Flynn but she found their differing ways of working hard to deal with. Davis was an actress always looking to improve her craft, whilst Flynn was too interested in partying for her liking. Davis said of Flynn:

‘For this particular role of a restless, confused newspaperman, he was well suited. Handsome, arrogant and utterly enchanting, Errol was something to watch.’

In turn, Flynn understood Davis’ star quality and admitted that ‘she was a far better actress than I could ever hope to be an actor.’

What makes the film work is the fact that they are the right actors playing the right characters. He is an arrogant, charming rogue to her powerful, driven woman, exactly as they were in real life.

Flynn the doomed hero: Dawn Patrol (1938)

Flynn and Rathbone were reunited in Dawn Patrol where they were joined by David Niven. The film centres around three members of the Royal Flying Corp during the Great War, with Flynn and Niven playing pilots who live for today, knowing that their chances of surviving each mission is getting slimmer.  Rathbone is the commander forced to send his men to certain death, labelled as a butcher and heading for a breakdown.

This is one of Flynn’s best films. With an anti-war message at its heart, he begins as a devil-may-care, charismatic joker, and the fact that he was acting the scenes of drunken revelry with his real-life best friend brings a natural comradery to the film. But when the responsibility of command is suddenly thrust on him, he changes. He begins to understand the weight that Rathbone had carried and when he is forced to send someone on a suicide mission he can’t do it. He goes himself and pays the price.

Flynn and Niven