There is a mad, bourgeois sadness to some of Jonathan Coulton's music. Weird Al Yankovic's music is parody and manic. Frank Zappa is just zany. Coulton, however, is a middle-class existentialist, where yuppies, monsters, and mad scientists mourn their decisions, lives, and madness.
A classic in this vein is "Shop Vac," whose yuppie protagonist brags on his suburban home with its separate bathrooms from his wife, his basement workshop, nearby gourmet grocery store, and multiple Starbucks, but he mourns the sad distance between himself and his wife, whom he can't hear crying upstairs. He emptily spends time in his basement, working his shop vacuum. They have no real friends in this place, which is hellish despite its outward appearances of middle class success.
In "The Future Soon," a school age boy mourns how the girl he has a crush on has rejected and embarrassed him, and he will have no time for her in his future as a mad scientist and world dictator. After he becomes a cyborg due to the robot war he initiates, she will reject him but he will always love her, and there are tones of regret at his inevitable actions. This theme gets repeated in "Skullcrusher Mountain," where the schizophrenic Dr. Moreau protagonist makes monsters. For the pretty girl he has kidnapped, he has made her a gift, this half-pony, half-monkey pet, so why is she screaming? Both this protagonist and the mad scientist in "The Future Soon" will destroy the world, and yet find themselves in love.
With "Code Monkey," a simian computer coder desperately wants a middle class life with a secretary from work, but it's all quite hopeless because, after all, he's some sort of monkey programmer. The protagonist in "Nemeses" is pleased at being trapped in a battle with his arch-nemesis throughout their normal lives. "Good Morning Tucson" shows the sadness of a weather reporter. "Ikea" sells "furniture for college kids and divorced men." "Chiron Beta Prime" features a trapped and dying family on a far-flung asteroid that tells of their sad Christmases there and begs for someone to visit them. "Mr. Fancy Pants" features a man who fights to have the best pants in the parade and loses. "I'm Your Moon" is the sad love story of Charon and Pluto, who orbit around each other in the dark end of our galaxy, misunderstood by our scientists. In perhaps the saddest of all, the giant sea monster of "I Crush Everything" lives a lonely life in deep parts of the ocean, watching the boats above and crushing everything it wants or loves, and never actually making contact with others.
This melancholic theme repeats in many of Coulton's songs where monsters, scientists, and the insane want a quasi-normal life and a person to love, or where a bourgeois protagonist mourns the emptinesses of his existence. (Walker Percy would approve.) There is this desperate nerdy need to fit into a normal life that Coulton returns to, and many of his fans deeply connect with this theme.
This melancholia culminates in what is something of an anthem for Coulton in his "A Talk with George," one of his own favorites from his many songs. Here the protagonist meets with George Plimpton, an American writer and mad adventurer who took mad chances in his zest for life. He is a cipher for Coulton himself, as Coulton left behind a computer programming job to be a full-time musician. As one who himself lived a middle-class, conformist life, gambled, and escaped it, Coulton's deepest sadness is this lost time, this misalignment of yourself in the world, and his melancholia is ultimately rooted in this bourgeois, conforming defeat. So if "there's someone else that you're supposed to be," then "shame on you if you don't set it free."