I know [Jim] talked about this and I cant quite remember, so I don't want to put words in his mouth, but I think it dealt with a human condition kind of thing, getting to the heart of something basically. It has this kind of similar sentiment to some of the other songs that deal with a question and the human condition, like this constant need for things and yearning and searching for stuff. And the Tootsie Pop reference is one of those things: getting to the prize, what do you have to do to get to that point.
Mike Mogis said the following about this song:
I know [Jim] talked about this and I cant quite remember, so I don't want to put words in his mouth, but I think it dealt with a human condition kind of thing, getting to the heart of something basically. It has this kind of similar sentiment to some of the other songs that deal with a question and the human condition, like this constant need for things and yearning and searching for stuff. And the Tootsie Pop reference is one of those things: getting to the prize, what do you have to do to get to that point.
Source: http://www.expressnightout.com/content/2009/09/monsters-of-folk.php