Lyric discussion by tommy crashwreck 

It's definitely "A hundred dollars makes the talking sad," as in paying a prostitute makes for depressing conversation. At least that's how I always hear/interpret the line.

Without a doubt, the lyric is "A hundred dollars makes it dark inside" - I've performed this song for years, and I just double checked in the Beautiful Maladies songbook.

@tommy crashwreck A hundred dollars makes it dark inside is what it is

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