Are we supposed to feel sympathy for a guy who has chosen to start a non-profit, has a loving wife, a nice house, a great son, and then whines about his life for most of the movie? I didn't. He is determined to make himself miserable by seeing nothing, but the lives of his buddies, who have seemingly been more materially successful.
He is taking stock of his life as he takes his smart, talented, decent son on his college tour, which includes his dream school, Harvard. (I am sick of Harvard being deified. Yale, Amherst, Williams, etc. are all viewed as lesser schools. They're not.)
In some ways, this is the modern, neurotic version of, "It's a Wonderful Life." A guy who has become bitter about his missed opportunities has the revelation that he's pretty lucky. But, somehow, Jimmy Stewart was charming. Ben Stiller is just irritating.
On one hand, he doesn't look down the social ladder to see how much better off he is than most people. He has a socially fulfilling job of his own making, not forced to work as a night janitor in an abattoir. And when he looks up the social ladder, he can only see an illusory world of wealth and happiness. It is beyond his imagination that people with more money - which is all he really knows about his old friends - can also be unhappy and unfulfilled. He doesn't know that there is "no there, there."
This is an aggravating, annoying movie. At one point, a young woman points out that his disappointment is really based on his white, male sense of entitlement. She says he should get pleasure from what he has done. I could barely contain myself from saying out loud, "Damn right!"
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