There is historical precedent for cross-dressing pirates. It’s also true that not all cross-dressers are gay, and that what constitutes male and female garb is somewhat arbitrary. (The only difference between a skirt and a kilt is societal norms). Mainly though, that scene was hilarious. If you’re worried about the normalization of the behavior, well, the movie seems to indicate clearly that it is abnormal.

I’m not sure where you are getting an indication that the movie is about masculinity. Do you mean the part where the narration says that Tristan progresses from boy to man in the story? What actually happens is that he gets over his crush on a carelessly cruel and vain girl, gains self-confidence, gets laid, gets married, and becomes king.

Tristan seems a little weak in the beginning because he has extremely good manners and lacks self confidence. The manners thing is a trope in fairy tales–the humble and polite people in these stories always come out on top. The lack of self confidence is just setup for his character arc. Tristan gains in confidence and assertiveness by the end of the film. He stands up to Victoria, Humphrey, and Steptimus. If Tristan didn’t improve during the course of the film and remained the same as he was at the beginning I would agree with you.

When is he running into all these women who solve his problems? He meets Yvaine who is a larger obstacle than a mere rock would have been. He gets a free ride from Primus, then meets Lamia who sees him as a pest to exterminate before she seizes a Star’s heart. Then he gets a ton of help from Shakespeare and his crew, followed by a run-in with another Ditchwater Sal who to turns him into a mouse. Near the end, he fights a bunch of witches and survives till the final one despite having no magical skills. Finally, Yvaine helps with the final witch. Now I’ll admit it would have been satisfying to see him simply stab Lamia, but on the other hand what happens makes sense. It should logically be nigh on impossible to kill the most powerful witch without magic of your own.

I’m also going to challenge the notion that all of the male characters (besides Shakespeare and Tristan) are evil murderers. Primus seems to be a pretty decent guy, just jaded from his upbringing. The soothsayer risks his life for the sake of the kingdom by intentionally feeding Septimus the wrong information. The goatherd is probably neutral at least. Shakespeare’s men are fine too. The wall guard seems to be a principled and dedicated guy! And Tristan’s own father is also a good man for keeping Tristan as a single father and apparently waiting for Una.

All-in-all, I think a rating of “Wokeish” for the unnecessary inclusion of a cross-dresser *might* be justified, but I don’t think that’s an open-and-shut case either. If that scene is trying to do anything besides be funny, it’s probably just demonstrating what tolerance should look like. Shakespeare is still captain because his “hobbies” don’t negate his skills, his charisma, or his experience and his crew recognizes this. I can imagine that he is good friends with some and that others owe him their lives–clearly their job is dangerous.

There’s a degree of cartoonishness to the depictions in the film as it’s intended to evoke fairy tales, but I would consider this at minimum a Woke-ish movie. More realistically, this is a fully Woke movie. It happens that I still enjoyed it, but I’m not afraid to acknowledge its clear political motives.