Song of the Day #3,226: ‘I Should’ve Known’ – Aimee Mann vs. Ben Folds Five

OK, here’s the first matchup in Round One of Montauk Madness that hit me right in the gut: Aimee Mann vs. Ben Folds Five.

Why hurt me like this, oh musical gods, by pitting two of my all-time favorite artists against each other in what should be the easiest round?

I discovered both of these acts right around the same time, 20 years ago. I know that because I gave their latest CDs (Mann’s I’m With Stupid and BFF’s Whatever and Ever Amen) to my brother-in-law as a birthday present in 1997.

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