Depressing Songs QUESTION

E-mail from a friend:

So there is this book called "I hate myself and want to die, the 52 most depressing songs you've ever heard" by Tom Reynolds

it is divided into chapters

1. I was a teenage car crash
2. I hate myself and want to die
3. I'm trying to be profound and touching but really suck at it
4. If I sing about drugs, people will take me seriously
5. She hates me, I hate her
6. Horrifying remakes of already depressing songs
7. I'm telling a story nobody wants to hear
8. I had no idea that song was so morbid
9. I mope, therefore I am
10.Perfect storms
Honourable Mentions

So I sat around in the Saratoga Last Vestige which is as close to High Fidelity as one is apt to get and 4 of us threw around songs and managed to guess over 20 of these songs and propose many others.

SOOO for the first thing I am making a set of CDs with the 52 most depressing songs of the book in order (from most depressing to the 52nd most depressing)

AND we are creating our own lists of 52 most depressing songs and combining them to make a second set of cds. And you are obviously the best qualified person I know to contribute to this endeavor. [Oh, the PRESSURE!] so please make a list. If you include any songs from the book I will let you know and you can submit another or submit 75 songs in order and i will just take the first 52 that qualify.

The book starts in the late 50s and goes to the present. My list is only going to go to the end of the 20th century unless i decide to include "White Flag" by Dido (I know I did horrible unforgivable things to you and that you can't possibly ever want to think of me again that is why I have decided to stalk you for the rest of your life and make you miserable all in the name of this perverted love I think I have for you).

OH and including a pithy explanation as to why you are including the song such as I just gave you above on white flag is appreciated but not required.

With an invitation like THAT how could I refuse?

So, off the top of my head I provided:

My Baby's the Star of a Driver's Ed Movie-Blotto (1) - "her underwear was clean"
Leader of the Pack-Melissa Ethridge (1, 6) - this one you certainly know, if not by this artist
The Needle and the damage done-Neil Young (4) -a paean to his dead friend
Abraham, Martin and John/What The world needs Now-Tom Clay (6,7)
Timothy-the Buoys (7,8) - cannibalism
1941 Mining Disaster-Bee Gees (3,7) - self-explanatory
Ebony Eyes-Everly Brothers (plane crash - yet hokey) - why is the plane late? maybe it left late. Can everyone waiting for the flight please report to the chapel?
People Who Died-Jim Carroll Band (3)- "they were all my friends and they died"; a Q104 staple
Tears in Heaven-Eric Clapton (7) death of his son
Strange Fruit-Cassandra Wilson (7) lynchings of black people; a Billie holiday song
I Am Rock, Richard Cory, Sound of Silence-Simon & Garfunkel; "I have my books and my poetry to protect me"; suicide; "hello darkness, my old friend"
The Mercy Seat-Johnny Cash death row
- indeed several songs from Folsom Prison - "shot a man in Reno just to watch him die"
to Sting's I Hung My Head - another shooting, followed by regret
Biko--Peter Gabriel (7) - death of anti-apartheid leader in South Africa

But I know there's a lot more, so I'll make you a deal. Send at least one song, preferably with a brief description, and I'll make you copies (if you want) of whatever uplifting music I receive from this project.
***
And speaking of free music, but not nearly so depressing, I still have a couple copies of my award-winning, Lefty Brown's Mixed Bag V disc exchange entry, Flick Tunes. Send me an address and I'll send you some tunes.
ROG