I take my inspiration where I can find it.
Recently, we started playing a GURPS game based (very loosely) on Heroes and heavily interlaced with GURPS' wonderful conspiracy-theory-laden Black Ops/Conspiracy X universe, enriched by years of paranoid embroidery by both of us, in various campaigns.
I don't know WHY certain characters have inspired certain songs to come to be. But we are slowly cobbling together a suite of songs named after the characters in the game (and some of the institutions of the game universe.)
These are the characters:
The Flying Librarian
The Electric Mechanic
The Invisible Hobo
The Millionaire Medium
While this arguably makes up the cast of Gilligan's Island, it also makes for a wonderful batch of inspiring kooks.
Take the Professor, for instance. He can understand what animals say... unfortunately for him, they cannot (always) understand what he says. This makes for some one-sided conversations. I built him a song around a sample of TMBG saying, "the words I'm singing now mean nothing more than meow to an animal." But then I took the sample out... it just wasn't working with the ambient groove I built to nest it in. It's better without it. (It is, however, very long... ambient songs always flow over the time I want them to exist within.)
The Electric Mechanic comes from a lovely rural farm family in the Midwest. I made him an alterni-pop little song just barely dark on the edges, thinking about his origins.
The Invisible Hobo is a homeless man with a saxophone and a history of tragic loss. I built him a song of beats and breaks, with some rather chirpy techno built in... and angry saxophone squeals weaving into the cacophany of the crescendo.
The Flying Librarian? I made something quirky of classically inspired samples and sassy electronica. I may scrap it and start again, but there's something very Flying Librarian about it.
The Wingnut made his own song. He featured some samples from a very funny, and characteristically insensitive, routine by the late, lamented, incomparable Sam Kinison.
The Messenger and the Millionaire Medium are yet to be immortalized in Deep Hurting song... although MC TV's Frank is working on one that I think is brilliant for the Messenger.
We are also doing songs for the Departments of the Company. If you know what I'm talking about, so much the better.
Anyway, if you want a preview... because they are most assuredly not finished, and need some major tweaking... well, here you go. Go forewarned... we ain't named Deep Hurting for nothing. And y'know, they're works in process, and all that.