Billy Joel/Tear Jerker

This legendary singer/songwriter has his fair share of song that can make one cry.

"And So It Goes" by Billy Joel. This song can affect anyone who is going through a tumultuous relationship with a loved one.

So I would choose to be with you
That's if the choice were mine to make
But you can make decisions too
And you can have this heart to break

Even grown men have cried at the end of "Goodnight Saigon" -- when all the voices, presumably of the soldier's lost comrades, join in with:

And we would all go down together.
Yes, we would all go down together.
We said we'd all go down together.

- Even more teary if you go to see one of his concerts -- when Billy does "Goodnight Saigon" live, he has all the roadies who were Vietnam veterans come out and sing with him on on that one bit.
And dear, God, "Lullabye (Goodnight, My Angel)".

Someday, we'll all be gone,
But lullabies go on and on.
They never die,
That's how you and I will be.

- Especially when combined with the video.
- There's also this live version, where Billy talks about his inspiration for the song and becomes so emotional he can't even get through the entire performance.
"Leningrad", which is based on a true story.

Victor was sent
To some Red Army town
Served out his time
Became a circus clown
The greatest happiness
He'd ever found
Was making Russian children glad
And children lived in Leningrad...

"Where's the Orchestra".

After all, this is my big night on the town
My introduction to the theater ground
I assumed that the show would have a song
So I was wrong...

This may be personal baggage, but "Vienna."
"James".

James...do you like your life,
Can you find release
And will you ever change,
When will you write your masterpiece.
Do what's good for you, or you're not good for anybody...James...

"Honesty" is a pretty good description of what it feels like to have a depressive meltdown. If you've been there, this song stings.

I can always find someone
to say they sympathize.
If I wear my heart out on my sleeve.
But I don't want some pretty face
to tell me pretty lies.
All I want is someone to believe.

"Tomorrow is Today", even more so because the lyrics were taken from Billy's suicide note.

Oh, my. Goin' to the river
Gonna take a ride and the Lord will deliver me
Made my bed, now I'm gonna lie in it
If you don't come, I'm sure gonna die in it.

"Piano Man".
"Always A Woman To Me"... especially if you've been in a relationship with someone who wasn't all that great to you, but you can't help but love them anyways.
Taken by themselves, "Stop in Nevada" and "If I Only Had the Words" are pretty depressing in their own right - the first is an elegaic song about a woman finally escaping her loveless marriage and terrible life for California, stopping in Nevada, but the song's melody implies that this, too, will be a mistake for her; the second is another slow song about how a man cannot explain everything he wants to towards the woman he loves, and can only offer physical comfort to her. However, the two songs are placed chronologically next to each other on the Piano Man album. Together, they can be seen as counterpoints to each other, and become about a billion times more depressing.