This is definitely a product of its time, but you still can't beat an Errol Flynn action movie.
Accused of treason for rendering medical care during the Monmouth rebellion, Dr. Peter Blood (Errol Flynn) is transported to the British colony of Jamaica to be sold as a slave. There he catches the eye of headstrong Arabella Bishop (Olivia de Havilland), niece to the largest plantation owner, who pays for him out of her own pocket. This does not endear Miss Bishop to the doctor, as he reckons his life worth more than pocket change. He gains a measure of autonomy by successfully treating the governor's (George Hassell) gout and uses it to put together plans for escape. Using the invasion of Spanish pirates as a convenient cover, Blood and his fellow slaves capture a ship and become buccaneers, earning enmity and admiration throughout the Caribbean.
This works best if you don't really think about it. Flynn has incredible charisma and de Havilland is as sharp as I've ever seen her. The humor still works, which is goddamn amazing considering how old this film is and it's not nearly as problematic as it could have been. Flynn does give a completely unironic speech about the evils of slavery at a time when Jim Crow laws and segregation were the de facto standard of the country that only gets cringier the more you think about it, but you can fast-forward through it and miss nothing about the movie.
It's currently streaming on HBO Max.
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