I agree. I think that few folks would rather be a homeless white dude than Oprah. But that’s not quite the right question.
Debaser, for the sake of argument, I’m going to assume you’re a middle-class straight white guy. And I’m going to make you a deal: you can exchange, not the identity, but simply the social status, of any of those three aspects of your identity. That is, you can trade the social status of being straight for the social status of being gay. Or you can change the social implications of being white for the social implications of being black.
How much would you be willing to pay to make that trade? Your choice which one.
Most straight folks wouldn’t be interested in paying anything to trade for the social status of being gay. Most white folks wouldn’t pay anything for the social status of being black. And so on.
So, fine. How much would I have to pay you to take on one of those statuses? Let’s leave everything else the same except for how folks would treat you if you were black. Sure–affirmative action fun is yours now! And you’ll get certain looks when you walk down the street at night! And taxi drivers will treat you like they treat black men! And when you walk into a business, you’ll be treated as if you were a black man! How much do I need to pay you to make that switch?
Scalzi’s “easy game settings” is a helpful way to think about it. There are all sorts of toggles on this game: play as a man (easier) or a woman (harder)? Play as a white person (easier) or a black person (harder)? Play as a straight person (easier) or as a gay person (harder)? Play as a rich person (easier) or a poor person (harder)?
If you move one setting, say, wealth, all the way to the “easier” end, you can move some other settings toward the harder end and still have an easier gameplay experience than someone who sets race and gender to white male but sets wealth all the way to the “harder” end.
But if you want to talk about privilege, you talk about just one setting. If you’re poor and homeless, would you rather be poor and homeless and a man, or poor and homeless and a woman?
There’s no question in my mind.