Shore up above

CINDERELLA (1950)

– How do I look?

– Stunning... as always.

It was more of a feminist, anti-toxic masculinity message: male vulnerability being rewarded, fake masculine facade being punished. With both the thugs and Flynn.

This is also why Flynn was failing miserably when he tried to use his dashing rogue exterior to get ahead in life and it was only when he chose to shed said exterior in the flooding cave, in what he believed to be their last moments, and revealed his real name and his vulnerability to Rapunzel that he started to triumph. It was a man being vulnerable - not dashing, not arrogant and not a male savior - that actually saved them both and prompted Rapunzel to remember she had magical glowing hair. It was not a magical girl TM moment, it was a human moment.

Obviously feminism - all waves of it - is intrinsically tied to politics but in this case the thugs segment was less about the left wing vs right wing propaganda and more about a woman - of a royal background, unbeknownst to her - feeling safe around unconventional men when they showed their sensitive and vulnerable side. Again, this applied to both the thugs and Flynn. Rapunzel saw them as untrustworthy before said vulnerable and protective side came out (smacking and threatening Flynn with the frying pan, hitting Hookhand with the tree branch using her hair and yelling at him). But immediately regarded their point of view when they treated her like an equal whom they were willing to share said point of view with.

I did some concept work for a Flynn

Rider prequel fan project ☀️ I wanted

to explore what his life was like as an orphan and how he became a thief.

You’ll see my ideas for what he looked like as a kid/teen/etc, some scenes from the noexistent prequel in my brain, and some art of the Trunchbull-like villain

In the movie it is largely ambiguous but Flynn does have a satchel with the Kingdom's sun emblem on it. Additionally, during the campfire scene he mentions how his childhood book hero, Flynnigan, could "go anywhere he wanted to go" whilst he was "a kid with nothing". Indicating he might have felt trapped in that kingdom where he knew mostly loss and oppression.

Storybooks take it further and some all but confirm that as a kid, Flynn/Eugene was indeed living in the "sun" Kingdom (Corona is not an official name as far as the movie timeline goes; as much as I don't like using anything series related it was, however, unofficially used by the movie creators in some interviews) and indulging his nerdy side throughout his childhood.

This illustration is from the Celebration of the Lost Princess storybook, set immediately after the movie events, where little Flynn/Eugene is immersed in a book with kingdom's emblem on it while other kids are playing outside:

In this magazine issue, "Once a thief", Rapunzel has a conversation with him that indicates that even as the "dashing rogue" he never got the chance to travel further than or outside the kingdom, even if he had seen most of it "on his travels". It's implied she drew that conclusion from Flynn's own stories and that he only told her of adventures limited to the kingdom:

Your version is consistent with the way the movie and post-movie materials handled his arc and, in the same vein, emphasizes his childhood struggles and abuses that were likely to occur when he was growing up at the orphanage. Explaining why he became disillusioned despite clearly growing up as an imaginative, hopeful kid (your illustration where he launches one of the lanterns is especially bittersweet/heartbreaking in that sense).