As I finish my most recent rewatch of Black Sails, I find myself coming back to this episode, with 2 of the best acted conversations I've ever seen put to film. The obvious, longer, eloquent-er one is Jack in the carriage. The other is here: 3 lines.

https://www.inverse.com/article/12518-black-sails-delivers-a-road-chase-with-a-twist/amp
Black Sails is a show about people caught up in the huge events of the world amd their ideas and pains withing that world. It's never really preachy, because it uses decisions and motivations of its characters to demonstrate these ideas in addition to saying then out loud.
We know they think this long before this conversation based on multiple actions we've seen them do. The actors have sold us on these two men's pasts, beliefs, & personalities. This exchange is a culmination of events, just like the show focuses on decisions driving consequences.
And spoiler alert, the final big exchange in the end of the finale is the same: how much comfort are people willing to sacrifice for their ideals? The two main actors have a rehash of this philosophical conversation, but with vast stakes.
Goddammit, watch black sails and listen to @BlackSailsCast
The last note I'll make: few film moments really get this much of an emotional reaction from me:

- Vane walking off the wagon of his own power

- Flint's breakdown over being called a monster

- Jack saying "get up" to Ann during that fight scene
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