Harry Chapin/Tear Jerker

This folk-rock artist is pretty much the master of tear-triggering songs.

"Cats in the Cradle" is definitely a tearjerker. The chorus was probably the most tearjerking part. The song is sung from the father's perspective, telling about his son and the fact that they never got to spend time together because of his work. Every time the son asks his father to play, the father answers with little more that vague promises that they will someday have a good time together.

And the cat's in the cradle, and the silver spoon
Little Boy Blue and the Man on the Moon
When you comin' home, dad?
I don't know when, but we'll get together then,
You know we'll have a good time then...

- Despite all this, the son looks up to his father, telling that someday he'll be just like him. Sadly, the father never did get to spend some time with his son. Time passes until the day his son graduated from college, and the father wants his son to sit down for a nice talk. This time, his son was too busy with his friends to do so and instead asks to borrow his car keys. Fast forward to present day, when the son has a family and house of his own. The father called his son, asking to visit. The son replied he can't because of his work and new family. The father then realizes that his son really did grow up to be like him. If you listen to it for a few times and keep the meaning of the song in mind, you'll probably cry.
"Mr. Tanner" is about a man who gives up everything to sing, which is what makes him feel whole, only to get poor reviews and his dreams crushed.
"Taxi".
"W.O.L.D."
"Shooting Star".
"A Better Place To Be" not really tearjerker material, until the final reprise of the chorus sinks in. That total loneliness, given a moment of silence, will make you sob.
"Sniper" Scary, yes. Haunting, yes. Heart rending, very. Anyone who has a dry eye after hearing this obviously didn't understand what the heck just happened.