Here's an interesting theme that stood out to me during my recent OFMD rewatch: the best way I can explain it is, being dumb is not treated as a vice. We see numerous ways that the characters are smart, observant, ahead of their time, etc., but that goes hand in hand with many moments of them also being delightful idiots. And by and large, the narrative doesn't punish them for it.
lol, Frenchie thinks cats are witches, and his flag is lame! But that cat flag becomes the British navy's blood-soaked symbol of the scourge that is the Gentleman Pirate and his crew. How's that for badass?
lol, Ed literally puts his life in the hands of dubious science--"The liver? We don't even know what that thing does!" But both he and Stede survive taking a sword on the left side with no lasting harm.
lol, the Swede wants to sing during the fuckery, that's not scary! But he does sing, it is scary, and Blackbeard himself praises his singing voice.
Note: being naive is a slightly different animal. Stede's naivete about piracy gets him in trouble more than once, like drinking nose juice or getting stabbed by the Spanish. This is especially true when he refuses to listen to people who know better. That said, he's still able to scrape through plenty of situations where he otherwise would have died.
We also see multiple instances of the characters treating each other kindly over something dumb.
When the Swede wants a little baggy to save his teeth in, the others don't laugh at him. Instead, Roach is gentle with him as he explains, "Thing is, Swede, teeth don't work like that. Once they're out, they don't go back in."
I just love this exchange between Frenchie and Pete: "Hey, this free drink shit is for the birds. You know what I mean?" "Birds love...drinking for free?" "No, that’s not what I mean. I mean, there's money to be made. Let's get our grift on." Frenchie's "no, that's not what I mean" isn't at all judgmental or mocking. It's just like, Oh, I see, you don't get it--let me say it a different way. He does, Pete understands, and they get their grift on! No harm, no foul.
For the most part, being dumb is only treated as something bad when it hurts others.
Stede and Pete's harmful assumptions about the indigenous tribe reinforce why they're in the cage and Oluwande isn't.
The crew's invasive and clueless questions about Jim's gender are met with anger and, in Frenchie's case, a knife at his throat.
The ignorant rich folks at the fancy party are very easily duped by Frenchie and Olu, then manipulated by Stede.
I can't quite explain why, but I really like that this is a show where being dumb is okay. It's fine for them all to be silly little guys. Their friends won't really think less of them for it, and they're still going to find a way to make it out alive. There's something so sweet about that.