Lyric discussion by songbirdjo 

Cover art for Wasteside lyrics by Regina Spektor

I'm pretty sure the song is making some reference to Sweeney Todd because of "all the barbershops and funeral-homes were open" and "then they'd get themselves a little hair cut and then promptly after they'd be dead" and the "drunk girl" she was referring to may have been Todd's wife Lucy who went insane and bothered everyone but they all ignored her. Not positive, but the lyrics just make me think of Sweeney Todd.

The town full of barbershops and funeral homes is an obvious reference to the russian 1928 book (or the 1971 cult film adaptation) Twelve Chairs, which is a satirical look at Soviet Russia. The book (and film narrative) both include the iconic line "The city of Stargorod ["old-city"] had so many barbershops and funeral homes that it seemed it's residents were born only for the purpose of getting a haircut, getting a shave, and then dying."