the olsen twins are a good choice- billionaires due to the choices of their exploitative parents when they were 3. but they're paying for it now in terms of mental health issues.

on a relately line of thought- joe simpson. you have a daughter with massive cans [see here] so you pimp her out in an unsettlingly pseudo-incestuous manner, then get your other daughter a nosejob and pimp her out as well, ending up with two multimillion selling singers with no discernible talent making preacher joe a thick wad of cash. undeserving.

oh- dan fucking brown. this guy had that unnerving ability to tap a vein of mediocrity that somehow bloomed into a pop culture phenomenon where it became hip for everyone to read the da vinci code. he's now rich as shit, and i have to put up with people who normally don't read anything more in depth than the instructions on the back of a two-minute noodles package telling me what a literary giant he is.

you could probably throw jk rowling into the mix, even though i've nothing against her, merely because no one should become a US$ billionaire for writing childrens books.