Most achingly-beautiful music

Wow! 17 years and still going. I gotta chime in
*Harry Belafonte - Take My Mother Home, Turn Turn, Scarlet Ribbons,      Danny Boy, Try To Remember
*Linda Ronstadt - Faithless Love, Long Long Time
*Eva Cassidy - Fields of Gold
*Left Banke - Walk Away, Renee (also Vonda Shepard)
*Indigo Girls - Down By The River (live)
*Many - Summertime, I think I lke Big Brother & the Holding Company best;   but Even Perry Como did a really nice version
* Cowboy Junkies - His Song/Her Song
*Concrete Blonde - Joey
* Isis (the old all girl band) - Rubber Boy
* Candy Stanton - He Called Me Baby
* Teresa Brewer - Let Me Go, Lover
* Bonnie Raitt - I Can't Make You Love Me
* Robert Plant & Alison Krauss - Killing The Blues

There are so many great recordings listed here I haven't read them all, so please excuse me if I duplicated any.

Iris Dement is another I hadn't heard of. This thread is costing me too much money. ;^)

Someone earlier had mentioned Alison Krauss' cover of Richard Thompson's Dimming of the Day. I love that version; but I think Bonnie Raitt's version suits me a tad better.
https://secondhandsongs.com/performance/8885/versions

Simon & Garfunkel - Bridge Over Troubled Water
Dusty Springfield-You Don't Have to Say You Love Me

Oh, Lang's "Constant Craving" is another fav.

@slaw ,

Great call.

Gotta get me some more Gillian Welch!

Here's another, as cosmic as lyrics come. I saw her do it live when she opened for Neil Young on his Greendale tour. What a show!

https://www.youtube.com/watch?v=CywArYObn2U

Emmylou Harris  - The Pearl
This may not be the best version.