Delicate
Damien Rice
2003

I just took a look at the rest of the list, and I'll just say that this will be one of your last "discoveries" that you get.

If you haven't listened to Damien Rice, repent, and start today.  So in 20 years, this Irish singer/songwriter has released exactly three albums.  Three!  That's it!  And each of those albums are masterpieces filled with just incredible, depressing songs.  I know, I know.  This is a list that inspires joy, but in order to feel that joy you have to have the bitter with the sweet.  (Now where have I heard this before?  Hmmm.) This guy is the absolute mountaintop for me when it comes to tapping into that melancholy.  And it's like going back in yesteryear with this guy, it's just magic.

If you haven't heard him, start with O, his debut album from 2002.  In my opinion THE best album of the '00s and quite possibly the best album in the last 20 years.  It is that good.  I discovered him completely randomly, while at a Virgin Records store in San Francisco on a random Saturday afternoon in 2002 as it was on an endrack as a "staff recommendation."  I just put on the headphones that were alongside and hit play and was immediately pulled in by this song.  (If you watched the tv series "Lost," this song was featured during the episode in the first season where Hurley finds his CD player on the beach.)

Quite honestly, if there was a single artist on my entire Top 100 list that I would recommend to you as an "artist to discover," this is the one.  And if you get the chance to see him live, definitely take advantage.  I would highly recommend this performance from a random hotel lobby in Germany eight years ago to give you a taste.  I could go on and on with Damien -- just stop what you're doing and get into this guy already!

Other Songs Considered:
Every single song in his catalog, but to start: Cannonball, The Blower's Daughter, I Remember, Elephant, Trusty and True, The Professor & La Fille Danse, Woman Like a Man