A friend of mine's wealthy grandfather just had a five-figure portrait commissioned of himself. And fair enough: Make a bajillion dollars, wrest yourself a bit of posterity. But why do portraits remain a favored purchase for those seeking to buy a bit of immortality? A hundred years ago, before Polaroids, maybe you wanted to preserve your visage, but that's hardly a tricky task now. The very fact of having a portrait of yourself is a status symbol, but that's only worth so much, and won't do much for your great-grandchildren's understanding of your impressive life and remarkable achievements and magnetic personality.
I've always thought that the next frontier in vanity industries should be commissioned biographies. Someone should set up a company employing out-of-work, or in-school, writers, and charge $30-$40,000 for beautifully bound, broadly positive, built-to-order biographies. They can even include some pictures. That way, you not only live forever, but get to control your story after you're gone. It's the perfect gift for the man who has everything but literal immortality.