This legendary singer/songwriter
has his fair share of songs that can make one cry
- If you live in or near the New York Metro area, his songs about the city will hit pretty close to home, especially "Miami 2017" and "New York State Of Mind."
- "And So It Goes". 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.
- "Lullabye (Goodnight, My Angel)". Especially when combined with the video.
Someday, we'll all be gone,
But lullabies go on and on.
They never die,
That's how you and I will be.
- 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...
- And, from later in the same song:
In that bright October sun
We knew our childhood days were done.
I watched my friends go off to war...
What do they keep on fighting for?
- "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...
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". For such a cheerful song it has a surprising amount of depressing imagery.
Now John at the bar is a friend of mine
He gets me my drinks for free
And he's quick with a joke or to light up your smoke
But there's someplace that he'd rather be.
- "She's Always A Woman"... 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.
- The sheer depression of "Allentown". Dead end jobs, dead end lives, and the slow decay of everything in the town from the factories to the people. And as if that weren't bad enough, the song ends with the narrator either dying or killing himself.
Well, we're living here in Allentown
And it's hard to keep a good man down
But I won't be getting up today
- From "Innocent Man", seeing someone pull away and into themselves, not because of anything you've done, but because they can't find the strength to trust again. And knowing you can't fix it because they won't let you.
I know you're only protecting yourself
I know you're thinking of somebody else
someone who hurt you...
I'm only willing to hear you cry
because I am an innocent man.
- "Downeaster Alexa", about a small Long Island fisherman who was finding it increasingly difficult to work the seas, particularly through commercial fishing fleets, restrictive policies and the conversion of his island home into a resort town.
Now I drive my Downeaster Alexa
More and more miles from shore every year,
Since they told me I can't sell no stripers
And there's no luck in swordfishing here.
I was a bayman like my father was before.
Can't make a living as a bayman anymore.
There ain't much future for a man who works the sea,
But there ain't no island left for islanders like me.