Jeff Buckley/Tear Jerker

Just the fact that neither Jeff Buckley nor his father lived long enough to really prove their talent can be a real Tear Jerker. A lot his own songs are also this.

Really, just about anything by him. Many of the songs are a bit melancholy already, but that voice of his could invoke tears just from its beauty.
"Lover, You Should Have Come Over", especially when you realize what the lyrics are at the beginning, can do it. It is best not to try picturing the scene that the lyrics are describing.

"Looking out the door I see the rain fall upon the funeral mourners
Parading in a wake of sad relations as their shoes fill up with water."

His raw utterances of "hallelujah!" in eponymous song are also prime Tear Jerker bait.
- In a "what if?" hypothetical based on what would probably happen if he didn't die in 1997, the image created was a frail eighty-year-old Buckley in a wheelchair in front of tens of thousands of fans -- moving just a little bit closer to the microphone so he could sing "Hallelujah" one last time.
- See also Leonard Cohen/Tear Jerker, who the song was written and originally performed by.
- As far as his covers go, his rendition of "I Know It's Over" also counts as well.
"Last Goodbye", definitely. "This is our last embrace, must I dream and always see your face?" So painful!
At his funeral, his mother played a recording of Jeff singing "Satisfied Mind", a song about departing from the earth with a happy conscience. That recording was later used as the last song on "Sketches For My Sweetheart the Drunk". When you hear it in that context, it's impossible not to think of the song as prime Tear Jerker.