This is based on opinion. Please don't list it on a work's trope example list.
Tear Jerker / Warren Zevon
"Keep Me in Your Heart", the last song he wrote and recorded just before his death, is this combined with heartwarming. And then Jorge Calderon covered it with a string quartet for the Zevon tribute album. Cue the waterworks.
In terms of lyrics, Hit Somebody (co-written by Mitch Albom), the story of a hockey goon, becomes this with a bit of awesome. No wonder Kevin Smith wants to turn it into a movie. A somewhat serious movie.
His cover of "Knockin' On Heaven's Door" on his album The Wind. Why is Zevon's version such a tearjerker? Zevon composed it when he knew he was terminally ill with cancer. The album was released two weeks before he died.
Then there is "My Ride's Here". Zevon also wrote that song as he was dying.
"Desperadoes Under the Eaves" can be depression inducing.
He got his diagnosis of terminal cancer before Life'll Kill Ya, and some places on that album you can hear him laughing about it, but the cover of "Back in the High Life Again," that he does, where there are a few places that something is clearly wrong with his lungs, and he knows he's lying, can reduce one to a quivering mess.
His final appearance on Late Show With David Letterman - in which he was the sole guest for the entire hour - about a year before his death, which was his final public performance. It's hard not to get misty-eyed seeing him play "Roland the Headless Thompson Gunner", the last thing he played on the show. After the end of the show, Zevon gave Letterman - a huge fan of his - the guitar he always played on the show.
A lot of his ballads can be considered this, including "Hasten Down the Wind", "Reconsider Me"note The liner notes for this song on the "Genius" album make it worse: She did. It was too late., "Accidentally Like a Martyr", "Mutineer", etc. Topping the list are the aforementioned "Keep Me in Your Heart" and "Knockin' on Heaven's Door", and ESPECIALLY a solo acoustic version of "Don't Let Us Get Sick" which he performed on Austin City Limits in 1999 and closes out both his love songs compilation "Reconsider Me" and the rarities/outtakes collection Preludes.
"The Indifference of Heaven." The title alone is depressing.
"I had a girl Now she's gone She left town Town burned down Nothing left But the sound Of the front door closing forever"
"The French Inhaler." It's the word Another that gets me, suggesting he's seen other women go through the same kind of bad experiences before.
"And when the lights came up at two I caught a glimpse of you And your face looked like something Death brought with him in his suitcase
Your pretty face It looked so wasted Another pretty face Devastated"