Most achingly-beautiful music

I could cite many, many examples, but here are three that stand out:

Eva Cassidy's version of "Over the Rainbow." A sublime performance of a classic song by an unbelievable singer. This one always gives me shivers.

"Can't Hardly Wait" by the Replacements. One of Paul Westerberg's best songs, wonderfully recorded by the great Jim Dickenson.

"Backstreets" by Bruce Springsteen. Incredibly dramatic and dynamic track, with a tour-de-force vocal performance. This is the song that really got me to start LISTENING to music -- noticing how a song was put together, arrangements, instrumentation, harmonies, dynamics, etc. They don't call him the Boss for nothing.

Jlindquist - You are right on with Cassidy's Over The Rainbow! I can tear up just thinking about how she sings it, let alone listening to her actually sing it. Makes Judy's version sound like the idle dream that little girls have. Eva's IMHO expresses the yearnings of a grown woman! Hard to believe it was a 'production' as opposed to something spontaneous! :-)

Ditto Satie's Gymnopedies 1-3; add Prince's, When You Were Mine and The Rolling Stone's, Moonlight Mile.

anyone heard any jerry douglas lately on a nice system .. ..severely wonderful Dobro guitar that can send you other places...also the grateful dead movie soundtrack..superb

Haven't been following this thread, so apologies if it has been mentioned. In terms of achingly beautiful, how about Patty Loveless "They Never Left Harlan Alive".