The rogueish Flynn Rider of Tangled looks somewhat apologetic here, which is possibly appropriate.
From the movie, at least, and also because he just seems like a guy that has a lot to apologize for.
It looks like the artist has captured Hercules pondering whether or not he really has what it takes to be a hero.
That, or he’s thinking about how rad it was that one time he killed the Hydra.
This one’s nice mainly because Naveen of The Princess and the Frog actually shows some other kind of emotion other than the staid princeliness of most of these other guys.
Seriously, Disney princes need to work on their emotional range.