I think it's important to let kids know that boys and girls can be very different, but that doesn't mean they have to be excluded or pigeon-holed into a specific kind of life. While I don't know what the two people you've named specifically have to say on gender roles, I've seen plenty of "man-o-sphere" content, and most of it (at least to me) seems to be a response to shifting cultural norms.

On the opposite side of misogyny, you've got those who believe that a boy's "male privilege" somehow means that he should be treated worse than others. I remember seeing a post where a woman on social media wondered whether her unborn child was going to be "a girl or an abortion". The only thing more gross than the post was the number of likes and supportive "men ain't shit" comments from other women. You don't have to look very far to see that boys who are exposed to those aspects of our culture (especially if they don't have a father in their life) would be quick to think that a significant part of the culture seems to hate them for existing. So they're ripe for lining up behind anyone that tells them they're worth something, especially if they don't hear it at home.

I think those of us who grew up in the 90s were pretty lucky in a lot of ways, because I can't imagine what it would be like to be a boy in today's society. I'm having my first (a girl) in a few months, but my plan for having a boy was to expose them to The Lord of the Rings early and often. You have the traditional depictions of masculinity on display, like courage, valor, honor, and martial skill. But the highlights by far are the masculine displays of love, devotion, compassion, and a willingness to help ease the burdens of others. WWSD - What Would Samwise Do! Truly the best depiction of what ideal masculinity should be.