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Cake – Short Skirt/Long Jacket Lyrics 18 years ago
I've always thought this song was satirizing corporate culture and the American lifestyle, and making a point of how they can suck the fun out of people.

The girl in the song is "changing her name from Kitty to Karen" (presumably because "Karen" is more conservative and professional-sounding) and trading in her European sports car for a white, American model with little character (but with cup holders for her morning commute!). Her life seems to be focused entirely on her career ("touring the facility and picking up slack", working long hours, dealing with red tape, and managing her finances).

Notice how her personality is never even mentioned in the song? The girl has "a mind like a diamond", "uninterrupted prosperity", jewelry, and shiny nails, but McCrea never mentions what she's like as a person. I think he's making the point that people tend to focus very heavily on others' monetary success, but they tend to forget things like, say...what they're actually like as people.

This song obviously relies very heavily on irony. It's pretty clear to me that he's using it to make a point; he doesn't actually want a girl who spends all her time working. Cake are known for their hatred of commercialism and corporate bloat, so it would be very out of character for them to idealize such a conservative and money-focused businessperson.

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