The Look I made a hat line is my favorite part of the song too...
You guys brought up a lot of interesting points. It is the first time in the show, he acknowledges any feelings for Dot, any upsetness/remorse for her leaving him. But then as Sean pointed out, he is immediately pulled back into his world of obsessive creativity.
He then sings about the two sides of being an artist: having to be remote from the outside world, but then sings about the passion of planning a sky.
It's definitely also about his preference for his artistic world of tranquility from the outside world, a point that is perfectly brought back in "Sunday." He sees both worlds, but accepts that his preference will lie with ihs own world of creativity before the warm world of human emotion. He also mentions that the only woman who could keep him in this real world is not the kind that will tolerate and wait around for him--Dot. The two worlds are referred to in the song: "Studying the hat/Enterting the world of the hat/Reaching through the world of the hat/Like a window/Back to this one from that." Back to this one from that is referring to both worlds.
And near the end of the song, George reconciles himself to the loss of Dot, recognizing that his world of creativity will always come before the world of human emotion, so he is incapable of giving himself to another human like Dot, and the childlike delight of look I made a hat is his being satisfied with his decision.
So simpler put, my interpretation is that this song is the moment of truth for George. Not that there was ever a danger of him choosing the world of human relations over art, but this is the moment where he ultimately decides, without a doubt, it will be the world of creativity, and so he must let Dot go, but again that last line...gah, the way it sums up the song...l know I'm repeating myself, but when he finally makes that decision, and says that line--it's his own satisfaction with it, that he is no longer torn, but knows where he belongs and is happy with it.
It's also interesting that...I'm pretty sure it's the songs Finishing the Hat and Art Isn't Easy that are derived from the same melody. In one song, the artist chooses to forego human relations to create, while in the other, the artist is bitching about all the human relations he must make, keep, and be in constant supervision of, in order to create. Very interesting contrast.
"If there was a Mount Rushmore for Broadway scores, "West Side Story" would be front and center. It snaps, it crackles it pops! It surges with a roar, its energy and sheer life undiminished by the years" - NYPost reviewer Elisabeth Vincentelli
