"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 to tear up at the gentle sweetness of it. "From out here, it's the rest of the world that looks so small..." 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!
He is better known for awesomely geeky songs, but When You Go is a very simple song about love and loss. Set to a memorial video for a fan's pet hedgehog, it's so sad and sweet.
Then there's "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.
"I Crush Everything". "This one's about a self-loathing giant squid." Sounds hilarious, don't it? 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."
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.
"Space Doggity":
Ignore the funny title (it's a homage to David Bowie's "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.
The third to last verse, where the scientists back home discuss the failure of the mission.
"It's a shame There is always something that gets compromised."
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."
The chorus, dear god. Especially the closing repetition:
Now I’m floating free And the moon’s with me And it’s bright enough To light the dark And it’s so high up here And the stars so clear Are they close enough Will they hear me bark... From here?
"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..."
From his 2011 album Artificial Heart we have Nobody Loves You Like Me. It's a haunting acapella tune with rather ambiguous lyrics about a man Drowning His Sorrows, and the most popular interpretation is that the singer is going through a divorce, but ends up Driven to Suicide at the end.
Blue Sunny Day. A lovelorn, death-seeking vampire experiences a brief, shining moment of happiness before daylight brings him down. Plenty of Lyrical Dissonance between the jaunty, bouncy music and the subject matter.
Today With Your Wife is a very melancholy song about a man spending the day with his (presumably) dead friend's wife. The song can also easily be interpreted as being sung by the man she's now seeing... which just makes it even sadder.
Shop Vac. A song about a suburban couple's life as it becomes, both implicitly and explicitly, increasingly banal and bleak.
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.
An equally likely (and still depressing) interpretation is one of someone at the end of their life, remembering deceased friends and hoping to join them as they pass away.
His cover of Leonard Cohen's "Famous Blue Raincoat." Helped by the fact that that's already the most depressing song in the world.
No matter how bad it gets, you can always look forward to Pizza Day.
Doesn't matter who you are, How your week has been so far, Cause you know when lunch time comes, That everything will be OK Hooray, pizza day Hooray, pizza day
"Mandelbrot set", especially since said professor who devised the setnote and provided countless contributions to the Chaos Theory and the song celebrates, Benoit Mandelbrot, passed away in 2010 from pancreatic cancer[1].
The music video for "All This Time" is a strange, sad Text ParserAdventure Game about a dystopian future factory worker and their suicidally depressed robot supervisor that ends with the worker removing the supervisor's vital circuit boards, causing him to die slowly and painfully.
is a very simple song about love and loss. Set to a memorial video for a fan's pet hedgehog, it's so sad and sweet.