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Liberty in Context
Dolly's full of libertarian-pleasing zingers like "no one said you have a right to happiness, just to the persuit of happiness". Plus she cheers everyone up instead of making them think they're depressed and go get meds.
That said, I can't see what is the point in engaging in Will's campaign to convince people that they are not as unhappy as psychiatrists tell them. (Or for that matter to convince them that they and we are happy.)
I think that Will protests too much. If people are so happy, then psychiatrists and public intellectuals are not going to convince them otherwise. He gives the impression of being worried that people really might be miserable if they stopped to think about it.
The real question is to what extent we can tell people are happy when so many of them are struggling to make ends meet and, as a consequence, don't have any time to ask if they are happy or not. The public intellectuals Will decries may be right that many people seem unhappy to others and would feel unhappy themselves if they reflected on what they were doing.
Leisure and solitude, I believe, have a tendancy to make people wonder if they are happy and to doubt it. What people with copious amounts of these goods think about how happy people are in general is interesting, but not ultimately decisive. On this, I agree with Will's critique.