[30 Day Song Challenge] Day 28: A Song That Makes Me Feel Guilty

This is an odd prompt. Is it meant to be a song that you feel guilty for liking — like a guilty pleasure? But that’s Day 13. I guess there’s a guilty pleasure that you’re gleeful about admitting and a guilty pleasure that you’d never admit. Like if you secretly loved singing the first stanza of Deutschlandlied while stretching out your right hand. Or, I guess, the prompt could mean that the song reminds you or forces you to feel guilty because of the content, the exhortation, of the lyrics. That could be Phil Collins’s treacly, if somewhat brilliant “Another Day In Paradise.”

But what about a song that is both a song that is supposed to make you feel guilty and a song that makes you embarrassed, makes you feel guilt or shame, for listening to it. I’ve got one: “Gypsy Woman (She’s Homeless)” by Crystal Waters. Not only is the song a rather oddly constructed tune about homelessness — it’s a house/disco song, and a classic one at that — but dancing to it makes you feel all icky. I mean, hello, you’re dancing to this peppy, joyful, beat-erific, singalong anthem at some club and it’s a song about a homeless woman who is doing all she can to keep up appearances. Yay! Twirl! Singalong! Have another cosmo! For a while, I’d sing along to the song at the clubs and laugh — oh, how ridiculous this song is — and now I can only gawk at the disconnect of the lyrics and the music.