Undertow was a bomb, yeah.
I get the impression that DGG is just doing what he wants to do. He did some commercials, too. I don't know whether there's any strategy of playing it safe or even necessarily delivering. His work seems to be the result of a very insular environment of old friends hanging out, tinkering around, seeing what they can get away with, doing what they think is funny. Whenever I've heard him speak, this seems to be the general vibe, even with things like George Washington and All The Real Girls. I think that he thinks that it's hilarious that he's in Ireland making a movie called Your Highness right now.
Personally, I admire that quality. I just have to not expect him to be great every time, but that each project would have a lot about it that are interesting because of his great taste and amazing sensitivity to environment. It's a bit like Soderbergh, though in a completely different style.
I love 'im.