You’re feeling bad and you’ll feel better eventually, but only after a good wallow. Go on, let it all out.

Miles Davis, “‘Round Midnight,” ‘Round About Midnight

This Thelonious Monk composition almost has a film-noir feel to it. The tempo picks up slightly after the melody plays, but don’t let that cheer you up. You can still feel plenty mournful.

Billie Holiday, “In My Solitude,” Lady Day: The Best of Billie Holiday

Billie knew a lot of sadness in her all-too-short life. This one’s for those times when you feel like being by yourself and really sitting in your melancholy.

Chet Baker, “Almost Blue,” Let’s Get Lost

I love Chet Baker. This is one of his later recordings and the vocals at the end reflect all the tumult he’d seen throughout his life.

**WILD CARD!!** Jude, “I Do,” No One Is Really Beautiful

Just try not tearing up when the cello solo kicks in. Gets me every time.