I'm surprised to see the lack of history here.
"Me & Bobbie McGee" was written by Kris Kristofferson, and kudos to him for making such a great song unisex.
"Stagger Lee" is ancient, dating back to at least the 50s in multiple versions.
http://en.wikipedia.org/wiki/Stagger_Lee The version mentioned in that article by PG&E is particularly chilling.
I'm surprised to see "Timothy" by the Buoys mentioned with the Rupert Holmes connection, but not "Him" or "Escape (The Pina Colada Song)". Rupert could milk it.
Rhino had an excellent LP of teen tragedy songs back in the mid 80s, complete with a Kleenex in the die cut cover made to look like a Kleenex box. They probably went to the same plant that did that Cheech & Chong album with the big rolling paper.
I couldn't find the Rhino album on the net, but here's a couple of albums of gems:
http://www.amazon.com/Last-Kiss-Songs-T ... B00004WIPK
http://www.amazon.com/Best-Tragedy-Vari ... B0000001A2
Jim Croce's got a lot, sure, but I'm also surprised to see the lack of Harry Chapin mentions. "30,000 Pounds of Bananas", "Taxi", etc. "Mr. Tanner" is beautifully tragic.
Mister Tanner was a cleaner from a town in the Midwest.
And of all the cleaning shops around he'd made his the best.
But he also was a baritone who sang while hanging clothes.
He practiced scales while pressing tails and sang at local shows.
His friends and neighbors praised the voice that poured out from his throat.
They said that he should use his gift instead of cleaning coats.
But music was his life, it was not his livelihood,
and it made him feel so happy and it made him feel so good.
And he sang from his heart and he sang from his soul.
He did not know how well he sang; It just made him whole.
His friends kept working on him to try music out full time.
A big debut and rave reviews, a great career to climb.
Finally they got to him, he would take the fling.
A concert agent in New York agreed to have him sing.
And there were plane tickets, phone calls, money spent to rent the hall.
It took most of his savings but he gladly used them all.
But music was his life, it was not his livelihood,
and it made him feel so happy and it made him feel so good.
And he sang from his heart and he sang from his soul.
He did not know how well he sang; It just made him whole.
The evening came, he took the stage, his face set in a smile.
And in the half filled hall the critics sat watching on the aisle.
But the concert was a blur to him, spatters of applause.
He did not know how well he sang, he only heard the flaws.
But the critics were concise, it only took four lines.
But no one could accuse them of being over kind.
(spoken) Mr. Martin Tanner, Baritone, of Dayton, Ohio made his
Town Hall debut last night. He came well prepared, but unfortunately
his presentation was not up to contemporary professional standards.
His voice lacks the range of tonal color necessary to make it
consistently interesting.
(sung) Full time consideration of another endeavor might be in order.
He came home to Dayton and was questioned by his friends.
Then he smiled and just said nothing and he never sang again,
excepting very late at night when the shop was dark and closed.
He sang softly to himself as he sorted through the clothes.
Music was his life, it was not his livelihood,
and it made him feel so happy and it made him feel so good.
And he sang from his heart and he sang from his soul.
(And) he did not know how well he sang; It just made him whole.
Oh, and don't forget "Voight" by Poster Children. "He came into the house like some deranged Cat In The Hat / Standin' over 6 feet 4 and carryin' a baseball bat."