Sad and Reflective Songs…

It just occurred to me as this came up, we don’t have a thread on really sad and reflective songs…

I’ll kick it off with this… We saw him play this live and it stopped the room for sure…

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Long Black Veil.
I saw someone cover it with a chorus backing them.
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A couple that immediately spring to mind:
Todd Rundgren - Bag Lady


The Eagles - The Last Resort

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Natalie Merchant - “My Beloved Wife”

Dustbowl Revival - “Got Over”

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Another Johnny Cash track that’s astounding is his cover of Nine Inch Nails’ “Hurt”

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We chose this song at my brother’s funeral - Brothers In Arms was the very first CD he ever bought, at age 17.

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How about almost anything sung by Phoebe Bridgers, my 20-something niece’s favorite singer and garment vendor. Wikipedia notes that

Her music has been described as “anxious,” “melancholy,” and “haunting.”

Here she sings Merle Haggard:

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She and Olivia Rodrigo (my late-teen kids are into her) sound very similar. That hyphen changes my statement drastically.

Talk about lack of dynamic range! I countered with Carmen McRae’s “Baltimore Oriole”.

Believe that’s Ben Webster on tenor sax.

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James Taylor - Millworker

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Simple but I find it very beautiful and, as requested, rather melancholy…

Oh, and I’d echo the Phoebe Bridgers recommendation by @Bill_Janssen and add Julien Baker:

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Some songs from Apartments are magic and touches me deep. Especially Twenty One, a song
about his son he lost at the age of three.

Perfect music for a bit of melancholy at night, with a beer, glas of wine or whisky.

Hope to see Peter Milton Walsh sing and play live once.

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