My recollection is that Chris Anderson's "Long Tail" never particularly promoted prosperity for those in the long tail but rather for the aggregators of the long tail. And that seems to have happened to a large degree.
Here's part of the blurb for Anderson's book:
Wired editor Anderson declares the death of "common culture"—and insists that it's for the best. Why don't we all watch the same TV shows, like we used to? Because not long ago, "we had fewer alternatives to compete for our screen attention," he writes. Smash hits have existed largely because of scarcity: with a finite number of bookstore shelves and theaters and Wal-Mart CD racks, "it's only sensible to fill them with the titles that will sell best." Today, Web sites and online retailers offer seemingly infinite inventory, and the result is the "shattering of the mainstream into a zillion different cultural shards." These "countless niches" are market opportunities for those who cast a wide net and de-emphasize the search for blockbusters.
That actually seems pretty accurate. Amazon and YouTube have done just fine by the long tail. And the variety of streaming services have pretty much fractured primetime network viewing and Top 40 radio. Power laws are still in effect and small-time artists are often doing even worse financially than they used to, and even some of the aggregators (e.g. Netflix) have their own struggles.