Sad Songs, They Say So Much

I haven't kept it a secret that Hawaii isn't my happiest place.  For various reasons that don't take years of psychological study to deconstruct, I spend a great deal of time being very sad.  I've gone through the stages of grief--replacing "acceptance" with the more pessimistic "resignation," of course--but grief is still there.  While any normal person would try to force themselves out of such a situation, look to the bright side, spank her Inner Moppet...whatever, I choose a different path:  I make a soundtrack.

A lot goes into putting together this kind of playlist, you know.  What actually constitutes a "sad song?"  Is it a song with a sad plot?  A threnody?  Is it a song that just reminds you of a really sad time in your life?  My operational definition is ineffable, it seems--Gestalt it is, then.  So here, for your listening pleasure, and in no particular order, I give you the eleven* saddest songs I can think of without spending an unreasonable amount of time on this.  (I chose to not include any tracks from operas or musicals, as that wouldn't be fair to any of the other genres.)

1. "Say Goodnight, Not Goodbye" (Beth Nielson Chapman) - I'll admit that the only place I've ever heard this song played is on "Dawson's Creek," but just try to listen to it without getting wistful.
2. "Last Request" (Paolo Nutini) - This song is probably technically about breakup sex; but breakups are sad, and this sadness is reflected in Paolo's voice.  Also, the version in the link is the only time where I was like, "okay, I can buy the fact that this guy is from Scotland."
3. "The Weakness in Me" (Joan Armatrading) - Ignore the thought of Heath Ledger stalking Julia Stiles as she pretends to play the guitar and listen to this sadness.  Also, this song is about infidelity, but she's clearly sad about it, so it's okay.
4. "Full of Grace" (Sarah McLachlan) - If I were actually ranking these, this might be the number one sad song.  It also took a lot of willpower not to make this a list of only Sarah McLachlan songs.  She pretty much is the master of songs to play on repeat whilst looking out the window and crying.  As such, here are her runners-up:  "Do What You Have To Do," "Good Enough," and "Wintersong."
5. "The Nicest Thing" (Kate Nash) - I love so many things about this:  the simplicity of the lyrics, the plaintive tone in Kate's voice, the strings.  Probably my favorite sad unrequited love song.
6. "Scientists" (Jeremy Messersmith) - This is one of those songs that's both inherently sad and sad because I relate to it so very much.  (Jeremy Messersmith runner-up:  "A Girl, a Boy, and a Graveyard")
7. "Falling" (The Civil Wars) - You all know how in love I've recently fallen with The Civil Wars.  Even if this song weren't about what it's about, it would still make you cry because it's that darn beautiful.  (Runner-up:  "Poison and Wine")
8. "You Don't Know Me" (Various Artists) - I had to include at least one of the standards on here!
9. "Delicate" (Damien Rice) - As extra-diegetic music goes, this one is a little over-used, but I feel that it's a good sad song.
10. "Lady" (Regina Spektor) - This song isn't particularly sad in the sense that it makes me want to cry, but I like everything that it does musically.  It's maybe the most threnodious song on my iTunes
11. "I Shall Believe" (Sheryl Crow) - Remember when Sheryl Crow was awesome?  You know, before she dated Lance Armstrong and before she turned into a pop star?  I like this ballad quite a bit.  

Don't get all worked up if your favorite "sad song" wasn't on this list or if your operational definition of "sad song" isn't the same as mine.  Again, there's too much complexity that you either have to exclude many things or include every thing, but if you have a suggestion, leave it in the comments.

Now if you'll excuse me, I'm going to go cry in a dark room while listening to all of these songs.


*Because I originally published it with ten and then thought of the eleventh one and felt too bad to bump any of the original ten.