Bruce Springstein - The River

This song is fucking beautiful; my personal favourite by Big Bruce and that's saying a lot. It's such a deep tale of how a young man fucked up his life by getting a young girl pregnant and then marrying her. The economy in the town runs dry and he has to work really hard to support his young family and had to say goodbye to all his dreams in life. The River drying up reflects this.

"Now I just act like I dont remember, mary acts like she dont care
But I remember us riding in my brothers car
Her body tan and wet down at the reservoir
At night on them banks Id lie awake
And pull her close just to feel each breath shed take
Now those memories come back to haunt me, they haunt me like a curse
Is a dream a lie if it dont come true, or is it something worse?"

^Dope as fuck, especially the last two lines.

Johnny Cash - Hurt

Despite what people might think Johnny Cash didn't write this song, but that doesn't change anything. The thing that makes this song so good is the way he sings it, the way his voice is riddled with such immeasurable sadness and pysichal affliction. Don't forget he was very very old when he sang this, and it was only a short time after his wife died. The way he plays the guitar and synchronizes it with the infinite sorrow in his voice makes this one of the greatest songs I've heard. Lyrically it's on another level, and was so appropriate to what he went through with his woman passing away.

"I hurt myself today, to see if I still feel
I focus on the pain, the only thing that's real
The needle tears a hole, the old familiar sting
I try to kill it all away, but I remember everything
What have I become? My sweetest friend
Everyone I know, goes away in the end
And you could have it all, my empire of dirt
I will let you down, I will make you hurt"

2pac - Wonder Why They Call You Bitch?

For me this is an overlooked classic by 2pac. Most people go on about Dear Mama and Until the End of Time but for me this is as good if not better, just because of how real it is. Brenda's Got a Baby is similar but it's a little too short in my opinion. This track is a classic and is very sad, just because of how real it is. It's tragic how many young women living in the slums see fucking rich men as the only way out of poverty. And it's equally tragic how many of them catch AIDS, lose everyone they ever loved, and die. This track deals this issue and although the title may raise a few eyebrows it's actually deep as fuck.

"I pass by can't hold back tears inside
Cause Lord knows, for years I tried
And all the other people on my block hate your guts
Then you wonda why they stare and call you slut.
It's like your mind don't understand
You don't have to kill your dreams plotting schemes on a man
Keep your head up, legs closed, eyes open
either a nigga wear a rubber or he die smokin'
I'm hearin' rumors so you need to switch
and niggas wouldn't call you bitch, I betcha."

Big Pun - Punish Me

For me this is the greatest love loss track ever written. It's not just lyrically amazing, it's word perfect, and there are hardly any tracks/songs that can be said about. Throughout the track he paints a subliminal picture of how he loved this woman and how she played him and used him for his money. Though that isn't the focal point of the track it's the bit that stands out the most. Not only does the bitch cheat on him she gives birth to his son and takes off with him, then has the audacity to beg his forgiveness. I'm sure many men can relate to this and know how painful these situations are.

"I was the luckiest man on earth, my wisdom was worth
Any purse but had a curse that hurt worse than givin birth
My first verse explains some of the game she was playin
Im blamin myself cause in my wealth was her pain would haven
Behavin like a money hungry hooker, funny how the money took her
From a average honey to a stunning looker
I look back and reminsce how we used to kiss
And smash hips in the gs I bought her last christ
She got too big for her britches but the britch is over
Not the one in queens I mean the one she dreamin wasnt sober
Told her how I felt, gassed me when she cried for help
Supplied the guilt trip and I was whipped without a fuckin belt
I felt stupid cupid struck me with a poison arrow
Shoulda drowned ya when I found ya crushin in my boys camaro
I didnt bother but you probably find your lover dead
You robbed me of my honor, you aint shit like my mother said"

Tracy Chapman - Fast Car

This is a sad song sang from the perspective of a woman who goes through a lot of shit and is in love with this guy who is obviously an asshole. First of all her dad becomes really ill so she has to skip school to look after him and because of it fucks up her education. Then when she gets older she meets this guy who is a lazy bastard and won't get a job so she has to work doubly hard and is stuck in the slumswith a dead dream that is going nowhere. Again this song is on the list because of how real it is. I'm not a fan of her singing but this song is extremely clever and is also very sad.

"You see my old man's got a problem
He live with the bottle that's the way it is
He says his body's too old for working
I say his body's too young to look like his
My mama went off and left him
She wanted more from life than he could give
I said somebody's got to take care of him
So I quit school and that's what I did
You got a fast car
But is it fast enough so we can fly away?
We gotta make a decision
We leave tonight or live and die this way"