ooh, tough question, Anon! I might actually have to rewatch the whole series to answer – how terrible! =D
From Season 1 – I really, really love the first episode. It just – sets the scene so nicely and it had my attention from moment one. And then of course we have 1×06 and 1×08, both of which were favorites of mine because there was just so much going on and I look back on them now and think wow – what a masterful job they did of setting up themes that were going to appear again in the show (not to mention that Flint spent a lot of those episodes being fascinatingly complex and awfully pretty).
And then we get into Season 2 and – well, where do I start with S2? It’s one of the best seasons for me personally, and I love all of it to tiny pieces, but my favorite episodes from it have got to be 2×01 through 2×05. I can’t choose between them, they’re all too good, I’m sorry, I’m claiming five favorites from this season instead of three, because there’s nothing about the London flashbacks that I don’t adore. It’s wonderfully politicky, and complicated, and heartfelt, and I adore that whole story arc. And then, of course, you have the fact that those episodes contain James Flint at his most amazingly intelligent and dangerous and really makes you understand why people fear and respect him.
Season 3 actually personally was not my favorite season, especially not at first. I like it better now, just it needed time to grow on me. I really, really love Flint’s speech to the Maroon Queen in 3×05 about “lives, loves, labor, spirits, homes,” because it’s everything that he believes in – literally everything, all in one speech. It’s the crux of what he’s fighting for, right there, and it’s a vision of a world that I find damn near impossible to look away from because it’s worth fighting for. Similarly, I love Vane’s speech in 3×09, because it’s a reminder that power derives from the consent of the governed, and that how we respond to fear is a choice, which I think is a powerful reminder we all need right now. Finally, last but certainly not least I love the tavern scene in 3×07, because that version of Long John Silver is the one that I recognize from Treasure Island. That is the man that had Billy Bones quaking in his boots twenty years on, and it really sets him up as Flint’s equal in rage and as the darker figure that he’d been growing into all that season. The John Silver that walked out of that tavern, book in hand, scares the shit out of me and that’s what he’s meant to do.
For Season 4, my favorite episodes have got to be, in order, 4×04, 4×02, and 4×10. I remember watching 4×04, getting to that part and sitting up, making an inhuman noise, and then going “WHAT??!!!!” They got me. They got me good, because I was about in the same place as James, thinking Thomas was dead and I’d never see him again in the series, and then they did that. It was a great moment. 4×02 I loved because – well, because that’s probably the last time I could like Woodes Rogers and Eleanor together even a little. For a little while there, they had something that was starting to be good, and I really, really felt for her when he left because there was just a sort of foreboding that she was never going to see him again. It was really well acted, it was heart-rending, and I also liked the talk that Jack and Teach had in that episode re: Vane and the conversation that Rackham had with Anne about Max. It was an episode with some really good character development. And then of course 4×10, you know why I like it already, but I’ll say this as well – I’ve never known an episode of a television show to affect me that deeply. That episode grabbed hold of me, shook me by the shoulders, and snapped, “wake up, damn it, it’s time to remember how to fucking FEEL things again!” And even if I don’t like 100% of the things that happened in the episode – even if they ripped my heart out of my chest and had it for dinner, pretty much – I can appreciate the power of the story they told and the way that it affected me and a lot of other people. I mean – it’s what, four months later, and we’re still arguing and crying and not ok as a fandom? That’s one hell of a story, regardless of how you feel about any aspect of it.