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Sometimes I Love It When You Break My Heart

25 Songs that are achingly, depressingly, painfully beautiful.
1Red House Painters
Mistress (Piano Version)

oh Mark Kozelek, I could put any of your songs on here... I'll put a Sun Kil Moon song on later.
2Talk Talk

That reverbed guitar lick at the beginning, just melts me dammit.
3Stars of the Lid
Tippy's Demise

When the violin breaks from the oscillating drone and runes down the scale. Yeah.
4Sufjan Stevens

Simple piano part and the ascending trumpet. Plus it's about the city of Flint, how depressing is that?
5Tom Waits
Georgia Lee

A gorgeous piano ballad. Some of the saddest lyrics I've ever heard.
6Ralph McTell
Streets of London

East Coast classic with some sad lyrics and great folk guitar.
7Bon Iver
Re: Stacks

Like I need to explain this.
8Sigur Ros
Untitled 3

Everyone knows the part that where the piano goes up an octave.
Motion Picture Soundtrack

The organ and Yorke tug your heart strings one last time.
10Pink Floyd
The Great Gig in the Sky

Vocal solo
11Okkervil River
So Come Back, I Am Waiting

It was between this, The Glow and A Stone but this epic pulls it out as the ending is just epic.
12Pepe Romero
Concierto Andaluz - Adaggio

Classical guitarists interpretation of the Rodrigo piece is at once technically marvelling and played with great emotion. The ending is fantastic as it symbolizes Rodrigo's stillborn baby rising to heaven with a picardy third.
13Neutral Milk Hotel
Two-Headed Boy Pt. 2

As if any list of this nature could be made without this song.
14The Decemberists
The Crane Wife 1 and 2

Not so much Pt. 1 as Pt. 2 with the breaking up "Heart" into a multi-syllabic cascade.
Repose in Blue

Great for night time driving
16Antonin Dvorak
Serenade for Strings

Dvorak is great and this serenade is incredibly pretty.
How It Ends

"And you already know. Yes you Aaaaaaalready know, how this will end."
18Godspeed You Black Emperor
The Dead Flag Blues

That monologue, that violin. Creep, beautiful, everything.
19Do Make Say Think

Their older stuff isn't my favourite, but this song is sweepingly cinematic and atypical beautiful for a band who take a more fun approach to post-rock then most other bands.
20Charles Spearin
Mr. Gowrie

The reverb drenched and backwords guitar bring a soft ambient undertone to a sad story of love from a Canadian immigrant
21Sun Kil Moon
Lucky Man

The guitar work is great and the vocal melody is among Kozelek's best.
22Billy Joel

So this is pretty cliche, but it's still a great song. It's also really fun and easy (unlike most of Joel's work) to play on piano.
23Andrew Bird

Especially the second half with the echoing drums.
24The Antlers

the vocal melody in the first half is equal parts catchy and depressing.
25Jeff Buckley

For very personal reasons, but even if I didn't have those reasons, this would still be a perfect fit to round out the list.
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