"I've Seen It All" by Bjork. Whether I hear the version with Thom Yorke or see it in the movie "Dancer in the Dark", I always remember the scene in the movie at which this song is sung (it was also nominated for an award - remember Bjork's outfit that year?) as the "feel good" moment in a very dreary, sad musical. Definitely bucks the tradition of peppy tunes in a peppy musical show!
"Life is Beautiful" by Sixx:AM. One man's journey through and out of heroin abuse and this song tells of his arriving clean on the other side. Most of the other songs in the album are dark and, as a recovering alcoholic myself and a big fan of Nikki Sixx's original band, this song makes me glad to be alive.
"The Little Things Give You Away" by Linkin Park. The lyric which talks about being six feet under water and looking up to "you" is the most haunting in this uniquely dark song in an album full of well-produced rage.
"Laughing With" by Regina Spektor. A list of incidences where no one laughs at God with a light twist in her practically trademarked yodel/yelp and a slaying last line of lyric.
"Dirty Little Secret" by The All-American Rejects. One of my favorite types of pop tunes - a toe-tapping beat in an easy-to-miss sad and dark lyric. One of the coolest videos of the decade for this song, btw. Really, anything that steers people to postsecret.com is cool by me.
"Rehab" and "You Know That I'm No Good" by Amy Winehouse. She has become the epitome of sad and dark in the lead-up to the award-winning album and her life in the years following that sudden fame. While "Rehab" is hook-filled 60's Motown-style pop, the other song of hers sounds the most to me like self-examination.
"Hurt" by Johnny Cash. If, indeed, there was a musical category called "wrenching", this version of Nine Inch Nails' morose ballad would be the godfather of this genre. Knowing Mr. Cash was so very close to the end of his life and career makes this song all the more . . uh . . wrenching. Cash, like the writer of this song, went through his own struggles with substance abuse. It's hard to think of any other perfect marriage of singer and songwriter, though both are all at once quite different and remarkably the same.