Song of the Day #3,367: ‘One for My Baby (and One More for the Road)’ – Frank Sinatra

After trotting out the songs that make us happy yesterday, you might have predicted that today’s installment of the 30 Day Music Challenge would call for ‘A Song That Makes You Sad.’

As a self-professed lover of melancholy music, I have no shortage of songs to choose from today. Many of my favorite artists (think Aimee Mann and Belle & Sebastian) are known for writing sad songs. But I decided to reach back to a classic from well before my time.

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