Lucky Me

pretty clearly this is a breakup song. Not just any breakup, but the kind that sends someone already prone to depression into a spin where they start thinking things like “I’ll jump off and take a drive” (I may be reading too much into that line, but not by much). It also has an attempt at optimism in lines like “Just think of what you’ll get when you’re past this,” but hearing the way this line is song, it’s clear that’s more of what she has to tell herself to keep going, rather then what she truly feels. The same goes for the first two lines (“How bad could it be, To be alone for now, To be free”), where she rhetorically asks a question the tone of the song answers. This gives the title line a bitter sarcasm.

A pretty dark song, on a pretty dark album from someone who’s not well known for singing dark songs because she usually sounds happier when she does it and most people don’t catch the lyrics (case in point, This, which sounds upbeat, but according to Lisa Loeb is, roughly, about reassuring a friend she wasn‘t going to kill herself).