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Errol Flynn, star of the Hollywood Golden Age, had his big break with a leading role in 1935’s Captain Blood. The womanising hedonist, who died at just 50 in 1959 while dating a 17-year-old, was a huge risk to Warner Bros being paired in a starring role opposite Olivia de Havilland, as both were relatively unknown.

The film, set in 17th century England, saw Flynn star as Dr Peter Blood who treats the wounds of a man injured in a rebellion against the Catholic King James II. As a result, Blood is sold into slavery in the Caribbean colony of Port Royal, Jamaica. Yet despite the kindness of his new owner, Olivia’s Arabella Bishop, he and his fellow slaves escape to become pirates. But when he crosses paths with her again years later, the swashbuckler hasn’t forgotten her compassion.

Flynn was so nervous about being in his first major starring role that director Michael Curtis had to reshoot his early scenes much later on in production. 

This plan worked out well as by that stage the actor had gained much more confidence, while Curtis would often drive him to do ten takes per scene. The star and the director would work together 12 times in total despite having an intense dislike of each other.

Meanwhile, Captain Blood was Flynn’s first of eight movies with Olivia, who he quickly fell in love with.

The leading lady, who died in 2020 aged 104, later admitted that she felt the same way, although both have denied having consummated the relationship.

She told PEOPLE: “There are no words to describe my feelings for Errol Flynn.” Nevertheless, this didn’t stop the cad from pranking her to the point of tears.

Flynn continued: “There was the time she found a dead snake in her panties as she went to put them on. She was terrified and she wept. She knew very well who was responsible and it couldn’t have endeared me to her. It slowly penetrated my obtuse mind that such juvenile pranks weren’t the way to any girl’s heart. But it was too late. I couldn’t soften her. Later she told me that she lived in terror of what bit of idiocy I’d spring next. Guess I haven’t changed much. Pranksters don’t. I must have spent too much of my early life with men. I had a lot to learn about the sensibilities of young ladies.”

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