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Tear Jerker: Michael Jackson
To everyone, his childhood. To his fans, pretty much his whole life.
"Little Susie". Made more poignant by the singing of a small girl at the beginning.
"Heal The World". It's sadder now that he's gone.
"Gone Too Soon" is a song written for Ryan White, an AIDS victim (due to a tainted blood transfusion) who was also one of the earliest advocates for research and acceptance of those afflicted with it. He and Jackson were friends for a while. MTV played it after Jacko himself died. And people all over wept.
"You Are Not Alone", "Man In The Mirror", "Earth Song", "Will You Be There" and "Cry". Made EVEN sadder when these songs (along with the aforementioned two) were played right after he was pronounced dead.
Then there are "She's Out of my Life", from the Off the Wall album.
In This Is It, the video for "Earth Song" has a little girl in a rainforest who dies trying to save a single flower from a bulldozer.
Disney Death: Might as well cry with relief. In an interview with the actress who portrayed the little girl, she mentions that in the actual concerts she was supposed to emerge to the stage, with the plant, alive.
For at least some of his fans, This Is It in its entirety is one big Tearjerker. This is as close to a Grand Finale tour as it'll get...and he never got to preform it live.
Once again, the song, "Childhood".
Also, "Ben". How much of a tearjerker this is may vary depending on whether or not you're aware that Ben is a rat. Not a scummy guy, a literal rat.
It is given even more poignant meaning after it was covered by Marti Webb as a tribute to Ben Hardwick, an infant who won a televised bid for a liver transplant, only to tragically pass away only a year after.
"Is It Scary". Especially for people who get made fun of because of their appearance.
To a lesser extent, "Threatened".
The breakdown of "Morphine," where the Industrial Metal drums suddenly cut off and are replaced with an orchestra, while Jackson comes as close as he ever could to outright confessing his addiction to painkillers. Because it was on one of his later, less-acclaimed albums, no one really noticed it until his later work was being re-evaluated after his death... from an overdose on painkillers.
This troper broke down crying when he finally heard the unreleased song "Someone in the Dark" from the ET The Extra Terrestrial Storybook Album on the same night he died. Not only does the song sound really sad but it's even sadder when one remembers his passing.