There are several songs that can make me cry.
Just recently I was at an event that featured part of a documentary on the Vietnam War and when the song “Ohio” came on — Ohio- Crosby, Stills, Nash and Young - YouTube — tears immediately started streaming down my face. I was only one year old and at the opposite end of Ohio when Kent State happened, but that song gets me right there.
If you think I’m sharing my box of Kleenex with you… . 
Having kids, this one
May your heart always be joyful
May your song always be sung
And may you stay
May you stay forever young
They grow up too fast
Dance with My Father by Luther Vandross is a very touching song.
One of Tom T Hall’s lesser known songs is Pay No Attention to Alice. It’s about an alcoholic wife. The line that gets me is “She cooked that chicken too long, but she don’t know that. Ah, what the hell. It ain’t too bad.”
If you grew up with an alcoholic parent, it just brings back all the disappointment and resignation you have to live with to accomodate that parent’s weakness. At least, it does for me.
On the instrumental side, there’s Scott Joplin’s Solace.
It’s his only tango. It sounds like a song trying to find happiness from a deep sadness.
You think that someday, there’ll be some sad song about a parent that stays glued to their iPhone?
Little Green by Joni Mitchell. It’s a song about giving up her daughter for adoption.
Solitude by Black Sabbath. It’s also one of the most beautiful songs in my collection.
the Mountain Goats - Matthew 25:21
Wherein the singer describes visiting his mother, who’s in the hospital dying of cancer. This year, it’s been 15 years since the death of my mother, and I haven’t been able to listen to that song once without breaking down into tears.
You were a presence full of light upon this Earth
and I am a witness to your life and to its worth
In the Ghetto - Elvis