I was raised to achieve. I was raised to think I was special and smart. But I was also disciplined. Severely. That's because I had the influence of my grandparents, and I'm actually thankful for that.
A lot of boomer parents were also irresponsibile because they were old hippies or old people who partied a lot, so there's that too, especially in the lower-income households. In fact, that's why my grandparents pretty much raised me...but I know people my age whose grandparents did not step in, who were raised with absolutely no structure or discipline or really proper care at all.
So there you have two extremes raised by the Boomers. One main complaint that I have in my daily life about Gen Y are the ones on the younger end have that crazy sense of entitlement, and they do have that more than Gen X or even older Gen Y-ers.
Something's wrong with every generation. But it's all connected, of course. People are products of the way they were raised and the culture they live in. So these problems are going to be complex.
All I can say on this topic is that I think Edie Sedgwick was a hell of a lot cooler than Paris Hilton. Take that however you will.