Aside from babysitting and mowing lawns for cash, my first actual job was working in the dishroom of a top-tier prep school. I also happened to be a student at the school and endured no end of comments and insults, but I wasn't getting cash in the mail every week or living on daddy's Amex card.
On the positive side, I learned almost every vulgar expression in the Spanish language.
Perhaps the worst experience in my first on-the-books-job: "Who the hell is FICA and why are they taking MY money?!?!"