I'm not sure I got this. Like the end song felt very "follow your dreams" for the same man who wrote Into the Woods. I guess it's supposed to be ironic? Also the guy who played the Balladeer in the recording I listened to had the complete wrong voice for the role. 
(Edit: i saw someone say that song was about the perversions of the American dream by extremists, not a pull yourself up by your bootstraps thing which makes more sense so I upped my rating by .25)