Big Old City

Like the good Professor Crispy at one point,  I've been listening to a lot of Taylor Swift.  While some of her songs are pretty mediocre (not a huge fan of Picture to Burn, for instance), when she hits it she really hits it - none of that awful obvious autotune or lyrics that perform absurd contortions to fit the beat.  Also: she's practically the only pop artist left who hasn't flirted with dubstep.

Crispy thought it was a male child speaking to an abusive father - at the risk of some armchair psychology, that's probably projection.  The music video tells a different story: a girl in small-town America, weathering bullies and saving up for college; sort of like a mini it-gets-better campaign.  Is the young girl with short hair who applauds at the end a representation of Taylor herself, imagining the joys of city life (seen in the Chicago-esque stage and performance)?  Probably, yes.

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Edited to add: after a few more listens, the 'child (of indeterminate gender) speaking to an abusive father' theory is starting to grow on me.  The references to alcohol, ranting in a bar, the probably-singular 'you' all conspire to prove me wrong.  My apologies, Professor.