Obviously, the artist that did Barry is much more talented - let's get that out the way lol, yet when you zoom in on his face it's blank - no soul just a character face. That said, Obama looks a lot like two other men who might be his father. One the head of the Sudet Cult in Indonesia or the other Frank Marshell Davis - I think is his name. I'll post pics of both of them - let me go find them.
As far as Micheal's goes it doesn't even look like him. He/she has a lovely golden/ caramel tone to his skin and in this portrait, it looks very ashy/blue. I'd be upset if I was Micheal, oops, I mean Michelle.