I think a big element in Louis C.K.'s success is the comprehensibility of what was presented to us.
He somehow made it very easy to figure out who he was, what his background was, what he was offering, what he thought was important, why he was doing this the way he was.
That made the personal "Am I $5 interested in this?" assessment an awful lot easier. In game-theory-ish terms, "What will I get out of this?" and "What''s he looking to get out of it?" were immediately answerable.
That's the first part: the scenario presented was readily comprehensible. This made him stand out from more typical offerings, which have obscure or uncertain motivations/personalities behind them.
The second important part of his success is that the answers to those questions were so positive - "He's a talented comedian who's selling his new show for $5", "He's an independent producer who's trying to be fair with his audience" "He's an ordinary person who trusts us to do right by him" - you couldn't help but become invested in his 'story' and want him to succeed in it.
And I think you can flip Louis' case and use it to show why Hollywood and the record labels are not doing so well in this post-scarcity market: Because it's not really clear what's the reasoning behind this piece of DRM, or the cost of this boxset, or any such moves. It's hard to know whether you're entering a fair transaction, what the person behind it wants for themselves.
And not only that, but to the extent that the motivations/personalities behind those offerings are comprehensible, it becomes clear that they're characters you'd rather deny than support.