(Debuted November 5, 1988, Peaked #60, 11 Weeks on the Chart)
Randy Newman has often written his songs with a tongue planted firmly in his cheek, so it's often hard to tell whether he's being sincere...or just being a smart-ass. He wrote Three Dog Night's 1970 #1 hit "Mama Told Me (Not To Come)," which was about an out-of-towner experiencing a Los Angeles party. His 1972 song "Sail Away" was a sales pitch to prospective slaves in Africa. And his biggest hit, 1978's "Short People," lampooned the idea that there was discrimination by taking the side of the person doing the discriminating to a ridiculous extreme. So...20 years into his career, it's easy to be jaded when listening to what he was writing.
That said, it's hard to listen to "It's Money That Matters" and not remember the way it was at the end of the Reagan Era. It was a high-powered time, a year after a stock market crash, an era where films like Wall Street and The Secret of My Success lauded the "win at all costs" business atmosphere of the Go-Go 1980s. At the same time, there was definitely a different feel for the working class.
In the song, the lyrics mention that there are people who are incredibly smart and barely eke by, and there are also successful men who do well despite the fact that they might not conform to the ideal. The big difference? The fat guy in the jumpsuit with a trophy wife had money. All the while, Mark Knofler lends his distinctive guitar riff in the background.