Songs by rich singers that imply that they're poor

Robbie Van Winkle?

Sorry, you said real rappers.

um, I think many of the “poor” guy songs are written before they made it big, or written with the memory of those days.

Many big rich rock stars spent years poor and struggling before they made it big, and probably find those days inspirational to thier writing.

Then, “Jenny from the block” just pisses me the fuck off…

Don’t be fooled by the rocks that I got,
I’m still, I’m still Jenny from the block.

No, JLo, you aren’t. You aren’t at all.

Not that Warrant was ever completely loaded, but they were already hitting it big when they released “32 Pennies.”

32 pennies in a Ragu jar
That’s all I’ve got to my name
But I love her and she loves me
To the pennies it’s all the same

Well, he was neither an astronaut nor a gay lawyer.

Just as an actor, a singer is often role-playing when singing a song. He’s using a persona, it doesn’t necessarily represent himself. Otherwise singers would be restricted to singing and composing songs only about their own lives, which, let’s face it, would be rather boring.

This cracked me up.

Well put.

What, BTW, might a “prize dairy cow” be? N.B. that unless I am mis-remembering, the “refrigerated storeroom” for the fur coats was actually more like an entire separate apartment in the Dakota.

I know nothing about the material possessions of John Lennon, so this is just a guess, but apparently he owned high quality dairy cattle. I Googled ‘“John Lennon” dairy cow’ and one of the results said it was Holsteins; another said Guernseys. Holsteins produce a lot more milk, but with less fat, than Guernseys.

Well Elvis grew up very poor, as did Johnny Cash, IIRC.

I don’t know if it’s really equivalent to a gated community, but Kanye West’s mom was a college English professor and he grew up in the Chicago suburbs. Not exactly hard core South Side.

ETA: Also, Kanye isn’t a gangsta rapper.

I was actually going to use Kanye as an example of how it’s now acceptable to be a middle class kid from the suburbs and rap. I think you can also classify Pharrell Williams in this grouping as well. And as Kyla notes, these dudes aren’t gangsta.

Dolly Parton is a nice example of the reverse. She sings about her poor childhood, and then about how fortunate she is now. (White Limozeen is one of my favorite of her songs, about the realization of big dreams and the material benefits that come along.)