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* "I'm Your Moon," described elsewhere on this very Wiki as "the most touching song about astronomical taxonomy ever written." Yes, it's quite literally about Charon trying to cheer Pluto up after being demoted to dwarf planet. But really, it's hard NOT tear up at the gentle sweetness of it. "From out here, it's the rest of the world that looks so small..."

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* "I'm Your Moon," described elsewhere on this very Wiki as [[OverlyNarrowSuperlative "the most touching song about astronomical taxonomy ever written." "]] Yes, it's quite literally about Charon trying to cheer Pluto up after being demoted to dwarf planet. But really, it's hard NOT tear up at the gentle sweetness of it. "From out here, it's the rest of the world that looks so small..."
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* Then there is [[http://www.jonathancoulton.com/mp3/Big%20Bad%20World%20One.mp3 Big Bad World One]].

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* Then there is [[http://www.jonathancoulton.com/mp3/Big%20Bad%20World%20One.mp3 Big Bad World One]]. What's this one about? Simply about giving up entirely under the weight of every bad thing the world can do to you.

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** "When You Go" can really affect those who have either lost loved ones, or have loved ones that are on the brink of death.



* "When You Go" can really affect those who have either lost loved ones, or have loved ones that are on the brink of death.
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*[[http://www.youtube.com/watch?v=XiNNkTbks24 Now I Am an Arsonist]], a touching, haunting song possibly about an astronaut receiving training, shooting for the moon, and exploding in the atmosphere.
-->Touch the sun\\
My eyes wide open, unbelieving\\
Catch a breath\\
The only one who's left is leaving\\
Now I am an arsonist.
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* "Space Doggity." Ignore the funny title (It's a homage to Space Oddity, obviously) this song is so depressing it's unbelievable. It's about [[http://en.wikipedia.org/wiki/Laika Laika]], the dog the Russians put in space and her last moments - and it's hard not to break down in tears. It hurts because it loves. What makes it worse is the third to last verse, where the scientists back home discuss the failure of the mission.

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* "Space Doggity." Ignore the funny title (It's a homage to Space Oddity, Music/DavidBowie's "Space Oddity", obviously) this song is so depressing it's unbelievable. It's about [[http://en.wikipedia.org/wiki/Laika Laika]], the dog the Russians put in space and her last moments - and it's hard not to break down in tears. It hurts because it loves. What makes it worse is the third to last verse, where the scientists back home discuss the failure of the mission.
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* [[http://www.youtube.com/watch?v=y4sOfO8Ei1g Shop Vac]]. A song about a suburban couple's life as it becomes, both implicitly and explicitly, increasingly banal and bleak.
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** Even more so when you know that Jonathan Coulton wrote this as a love song to his daughter, and when he plays it at concerts, it's always preceded by an introduction about becoming a first-time parent.
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** Personally, I think it's more heartbreaking in the verses sung from ''Laika's'' point of view, alone and dying in space. "I don't think I want to be a good dog anymore." *sniffle*

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** Personally, I think it's Although, it may be more heartbreaking in the verses sung from ''Laika's'' point of view, alone and dying in space. "I don't think I want to be a good dog anymore." *sniffle*
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** "You Ruined Everything." The title makes it sound like a [[NonIndicativeTitle particularly bitter break-up song.]] The actual lyrics?

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** * "You Ruined Everything." The title makes it sound like a [[NonIndicativeTitle particularly bitter break-up song.]] The actual lyrics?
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* Possibly his most bittersweet song ever, [[http://www.jonathancoulton.com/wiki/You_Ruined_Everything You Ruined Everything]] is a song about how having a child completely destroys everything in your life, and how much you can resent them for it... all the while as you love them more than anything on the planet and would never, ever give it up. It's both tearjerking and heartwarming at once.
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** Not necessarily friend; the song can equally easily be interpreted as being sung by the man she's now seeing... which just makes it even sadder.
* Possibly his most bittersweet song ever, [[http://www.jonathancoulton.com/wiki/You_Ruined_Everything You Ruined Everything]] is a song about how having a child completely destroys everything in your life, and how much you can resent them for it... all the while as you love them more than anything on the planet and would never, ever give it up. It's both tearjerking and heartwarming at once.
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** Personally, I think it's more heartbreaking in the verses sung from ''Laika's'' point of view, alone and dying in space. "I don't think I want to be a good dog anymore." *sniffle*
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** In his series of blog posts about the fifth-year anniversary of his Thing a Week project, he noted how a song he'd only given a little bit of thought to had exploded beyond its boundaries. Although he ''wrote'' the song about Pluto and Charon, the ways in which people had been using it--as a song at their weddings, as a lullaby for their children--had made it into so much ''more.'' And he thinks that's awesome. So he's acknowledged its power himself, and just knowing how much the song has struck a chord with people is tear jerker in itself!

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* From the as of yet unreleased album Artificial Heart we have [[http://www.youtube.com/watch?v=zlGDnvWQpII Nobody Loves You Like Me]].

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* From the as of yet unreleased his newest album Artificial Heart we have [[http://www.youtube.com/watch?v=zlGDnvWQpII Nobody Loves You Like Me]].


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* [[http://www.youtube.com/watch?v=Q-BM_ig-FRY&feature=related Today With Your Wife]] is a very melancholy song about a man spending the day with his ([[WildMassGuessing presumably]]) dead friend's wife.
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-->"Moscow to Sputnik 2\\
I think we're losing you ... "

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-->"Moscow to Sputnik 2\\
I think we're losing you ...
-->"It's a shame\\
There is always something that gets compromised.
"
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Respectfully, I don\'t think that was the intent of the cover. Most likely, he, like The Dan Band before him, discovered the inherently humorous prospect of a man singing a song obviously for women.


* [[http://www.jonathancoulton.com/2007/04/19/you-oughta-know/ His cover]] of Alanis Morrissette's "You Oughta Know" turns it from a sarcastic song from the perspective of an angry and bitter woman to a ''freakin' depressing'' song from the perspective of a sad and bitter gay man who got dumped for a woman.
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* [[http://www.youtube.com/watch?v=K_1uK67mQm0 Blue Sunny Day.]] A lovelorn, death-seeking vampire experiences a brief, shining moment of happiness before daylight brings him down. Plenty of LyricalDissonance between the jaunty, bouncy music and the subject matter.

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-->"Moscow to Sputnik 2 \\I think we're losing you ... "

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-->"Moscow to Sputnik 2 \\I 2\\
I
think we're losing you ... "

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-->"I don't think...\\
I wanna be a good dog anymore."

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-->"I don't think...\\
I wanna be a good dog anymore.
-->"Moscow to Sputnik 2 \\I think we're losing you ... "
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* From the as of yet unreleased album Artificial Heart we have [[http://www.youtube.com/watch?v=zlGDnvWQpII Nobody Loves You Like Me]].
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* "Womb With A View," a very gentle, almost bittersweet song about two "artificial wombmates" culminating in one being born into the world and wondering if the bond they've shared will last.
-->"Maybe when we get outside, we'll both still remember\\
Maybe someday we will meet on the street, and I'll know it's you..."
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* Space Doggity. Ignore the funny title (It's a homage to Space Oddity, obviously) this song is so depressing it's unbelievable. It's about Laika, the dog the Russians put in space and her last moments - and it's hard not to break down in tears. It hurts because it loves. What makes it worse is the third to last verse, where the scientists back home discuss the failure of the mission.

to:

* Space Doggity. "Space Doggity." Ignore the funny title (It's a homage to Space Oddity, obviously) this song is so depressing it's unbelievable. It's about Laika, [[http://en.wikipedia.org/wiki/Laika Laika]], the dog the Russians put in space and her last moments - and it's hard not to break down in tears. It hurts because it loves. What makes it worse is the third to last verse, where the scientists back home discuss the failure of the mission.

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-->"I don't think/I wanna be a good dog anymore."

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-->"I don't think/I think...\\
I
wanna be a good dog anymore."

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Removing first person references and personal anecdotes...


* "I'm Your Moon," described elsewhere on this very Wiki as "the most touching song about astronomical taxonomy ever written." Yes, it's quite literally about Charon trying to cheer Pluto up after being demoted to dwarf planet. But really, this troper can't NOT tear up at the gentle sweetness of it. "From out here, it's the rest of the world that looks so small..."

to:

* "I'm Your Moon," described elsewhere on this very Wiki as "the most touching song about astronomical taxonomy ever written." Yes, it's quite literally about Charon trying to cheer Pluto up after being demoted to dwarf planet. But really, this troper can't it's hard NOT tear up at the gentle sweetness of it. "From out here, it's the rest of the world that looks so small..."



* This troper first heard it recently. He cried. Since you beat him to the punch, we also have [[http://www.jonathancoulton.com/mp3/Big%20Bad%20World%20One.mp3 Big Bad World One]].
* This troper sang "When You Go" to her best friend dying in hospice, and can't even think about the song now without tearing up.
* . This troper's friends played "when you go"(among other songs) on his 19th birthday. This troper's friends saw a person ,who has coldly beat down and break more than a staggering amount of men, breakdown and cry like a newborn.This was the day after this troper learned his child was miscarried.
** [[http://www.youtube.com/watch?v=zsV-qozMz9A Oh lord why]].
*** DAMN YOU, I HAD JUST GOTTEN OVER THAT ONE. I used to be made of STONE, man.
** I Crush Everything. "This one's about a self-loathing giant squid." Sounds hilarious, don't it? ''Wrong.''

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* This troper first heard it recently. He cried. Since you beat him to the punch, we also have Then there is [[http://www.jonathancoulton.com/mp3/Big%20Bad%20World%20One.mp3 Big Bad World One]].
* This troper sang "When You Go" to her best friend dying in hospice, and can't even think about can really affect those who have either lost loved ones, or have loved ones that are on the song now without tearing up.
* . This troper's friends played "when you go"(among other songs) on his 19th birthday. This troper's friends saw a person ,who has coldly beat down and break more than a staggering amount
brink of men, breakdown and cry like a newborn.This was the day after this troper learned his child was miscarried.
** [[http://www.youtube.com/watch?v=zsV-qozMz9A Oh lord why]].
*** DAMN YOU, I HAD JUST GOTTEN OVER THAT ONE. I used to be made of STONE, man.
** I
death.
* "I
Crush Everything.Everything". "This one's about a self-loathing giant squid." Sounds hilarious, don't it? ''Wrong.''''Wrong''.



--->''You should know''
--->''How great things were before you''
--->''Even so, they're better still today''
--->''I can't think of who I was before''
--->''You ruined everything''
--->''In the nicest way.''
** This troper hates you all for making her cry like a little bitch.

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--->''You -->"You should know''
--->''How
know\\
How
great things were before you''
--->''Even
you\\
Even
so, they're better still today''
--->''I
today\\
I
can't think of who I was before''
--->''You
before\\
You
ruined everything''
--->''In
everything\\
In
the nicest way.''
** This troper hates you all for making her cry like a little bitch.
"



* Space Doggity. Ignore the funny title (It's a homage to Space Oddity, obviously) this song is so depressing it's unbelievable. It's about Laika, the dog the Russians put in space and her last moments and it never fails to make this troper break down in tears.
** It hurts because it loves. What makes it worse is the third to last verse, where the scientists back home discuss the failure of the mission.
** This Troper always tears up at "I don't think/I wanna be a good dog anymore."

to:

* Space Doggity. Ignore the funny title (It's a homage to Space Oddity, obviously) this song is so depressing it's unbelievable. It's about Laika, the dog the Russians put in space and her last moments - and it never fails it's hard not to make this troper break down in tears.
**
tears. It hurts because it loves. What makes it worse is the third to last verse, where the scientists back home discuss the failure of the mission.
** This Troper always tears up at "I -->"I don't think/I wanna be a good dog anymore."
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* . This troper's friends played "when you go"(among other songs) on his 19th birthday. This troper's friends saw a person ,who has coldly beat down and break more than a staggering amount of men, breakdown and cry like a newborn. why?This was the day after this troper learned his child was miscarried.

to:

* . This troper's friends played "when you go"(among other songs) on his 19th birthday. This troper's friends saw a person ,who has coldly beat down and break more than a staggering amount of men, breakdown and cry like a newborn. why?This This was the day after this troper learned his child was miscarried.
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* . This troper's friends played "when you go"(among other songs) on his 19th birthday. This troper's friends saw a person ,who has coldly beat down and break more than a staggering amount of men, breakdown and cry like a newborn. why?This was the day after this troper learned his child was miscarried.
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** This Troper always tears up at "I don't think/I wanna be a good dog anymore."

to:

** This Troper always tears up at "I don't think/I wanna be a good dog anymore.""
----

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** I Crush Everything. "This one's about a self-loathing giant squid." Sounds hilarious, don't it? ''Wrong.''** "You Ruined Everything." The title makes it sound like a [[NonIndicativeTitle particularly bitter break-up song.]] The actual lyrics?
---->''Youshould know''
---->''How great things were before you''
---->''Even so, they're better still today''
---->''I can't think of who I was before''
---->''You ruined everything''
---->''In the nicest way.''

to:

** I Crush Everything. "This one's about a self-loathing giant squid." Sounds hilarious, don't it? ''Wrong.''** ''
**
"You Ruined Everything." The title makes it sound like a [[NonIndicativeTitle particularly bitter break-up song.]] The actual lyrics?
---->''Youshould --->''You should know''
---->''How --->''How great things were before you''
---->''Even --->''Even so, they're better still today''
---->''I --->''I can't think of who I was before''
---->''You --->''You ruined everything''
---->''In --->''In the nicest way.''



** This Troper always tears up at "I don't think/I wanna be a good dog anymore".

to:

** This Troper always tears up at "I don't think/I wanna be a good dog anymore".anymore."
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* "I'm Your Moon,", describe elsewhere on this very Wiki as "the most touching song about astronomical taxonomy ever written." Yes, it's quite literally about Charon trying to cheer Pluto up after being demonted to dwarf planet. But really, this troper can't NOT tear up at the gentle sweetness of it. "From out here, it's the rest of the world that looks so small..."

to:

* "I'm Your Moon,", describe Moon," described elsewhere on this very Wiki as "the most touching song about astronomical taxonomy ever written." Yes, it's quite literally about Charon trying to cheer Pluto up after being demonted demoted to dwarf planet. But really, this troper can't NOT tear up at the gentle sweetness of it. "From out here, it's the rest of the world that looks so small..."
Is there an issue? Send a MessageReason:
None


* "I'm Your Moon," by JonathanCoulton, describe elsewhere on this very Wiki as "the most touching song about astronomical taxonomy ever written." Yes, it's quite literally about Charon trying to cheer Pluto up after being demonted to dwarf planet. But really, this troper can't NOT tear up at the gentle sweetness of it. "From out here, it's the rest of the world that looks so small..."

to:

* "I'm Your Moon," by JonathanCoulton, Moon,", describe elsewhere on this very Wiki as "the most touching song about astronomical taxonomy ever written." Yes, it's quite literally about Charon trying to cheer Pluto up after being demonted to dwarf planet. But really, this troper can't NOT tear up at the gentle sweetness of it. "From out here, it's the rest of the world that looks so small..."

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