Zar

Matthew Good, formerly of the Matthew Good Band, has done some rather depressing songs in his time. He's relatively unknown here in America though, as he's Canadian.

Some of his more depressing songs include Suburbia, Fated, Running for Home, The Fine Art of Falling Apart, A Boy and his Machine Gun, My Life as a Circus Clown, The Rat who would be King, and Going All The Way.

Now that I think of it, most of Matthew Good's songs are depressing =p. Good stuff nevertheless.

Edit: Just thought of another artist with a tendency to depress the hell out of you, Aimee Mann. Just about all of her stuff will make you want to bawl your eyes out, but "Wise Up" takes the cake.

Wise Up

It's not
What you thought
When you first began it
You got
What you want
Now you can hardly stand it though,
By now you know
It's not going to stop
It's not going to stop
It's not going to stop
'Til you wise up

You're sure
There's a cure
And you have finally found it
You think
One drink
Will shrink you 'til you're underground
And living down
But it's not going to stop
It's not going to stop
It's not going to stop
'Til you wise up

Prepare a list of what you need
Before you sign away the deed
'Cause it's not going to stop
It's not going to stop
It's not going to stop
'Til you wise up
No, it's not going to stop
'Til you wise up
No, it's not going to stop
So just...give up