Britney Spears/Tear Jerker

This pop singer has some rather emotional songs.

"Everytime". May be, in fact, the ultimate loss of love song ever.

At night I pray
That soon your face
Will fade away

"He About To Lose Me".

I'm Touching hands with someone seriously beautiful

"Out From Under" is also very much a tearjerker, especially when you put it into the context of her recent divorce with Kevin Federline and all of the trouble she went through as a result of it.

"I don't wanna dream about
All the things that never were
And maybe I can live without
When I'm out from under
I don't wanna feel the pain
What good would it do me now?
I'll get it all figured out
When I'm out from under"

"I Run Away"

maybe when time goes by, I'll understand

Where Are You Now.

I can hear your voice, The ring of yesterday
It seems so close to me, But yet so far away

And "Shadow" in a similar way to "Where Are You Now"
The music video for "Lucky" where we follow the famous actress through a day in her life and see that, despite all she has, she is truly empty. The video ends with the actress crying herself to sleep with the knowledge she has to get up the next day and do it all again. Even sadder now coupled with Harsher in Hindsight.