Chris Anderson's Wired article was a major influence in the development of Adobe Media Player. He has written only a handful of blog posts about the combined subjects of the long tail and internet television, which I'm just now finding and reading.
In early 2005, Chris Anderson wrote:
...Both the channel-centric reality of TV and its ephemeral nature are artifacts of the distribution bottleneck of cable broadcast. TV is still in the era of limited shelf space, while the lesson of the Long Tail is that more is always better. The growth of cable capacity over the past decade pales next to the growth in video creation over the same period and the size of the potential microaudiences for anything and everything. TiVo may have helped by at least taking the tyranny of time out of the equation, but we are nowhere near the iTunes model of being able to download everything ever made, anytime. There are several reasons for this. First, TV has some gnarly rights issues. Content is locked up in all sorts of ways, starting with broadcast network carriage agreements and finishing with syndication. Then there are the costs of streaming high-quality video, which amount to about $2 per hour. Finally, and perhaps most importantly, there is the small matter that most TV is free to viewers, subsidized by advertising. It's not clear how to make downloaded video a good medium for advertising, given that you can't know in advance when it will be seen and TiVo-trained viewers are getting all too good at ad-skipping.
Since then, many things have changed. Premium content owners have battled back against DVRs and torrenters by offering on-demand playback of their full episodes online, while streaming costs have dropped dramatically. And most significantly to Chris's point, Adobe Media Player 1.0 tackled the core problems concerning offline ad playback, measurement, and relevancy around downloadable video content.
But there are other, larger issues to deal with here.
The Long Tail: Long Tail TV: Part III
...I spent some time with Howard Look, who runs TiVo's applications and interface team. He was kind enough to run some numbers on TiVo users' behavior based on what they've got programmed as season passes. The first chart shows the percentage of users who have any of the top 100 shows programmed to record. The second extends that to the top 7,000 shows, averaged over windows of 100 shows (click for larger versions).
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What these charts show is that the top 24 season passes make up 25% of total season passes, and the top 80 season passes make up 50% of the total season passes. But what that means is that the bottom 6820 season passes make up the other 50%. In other words, the Tail is about the same size as the Head. Which is exactly the same ratio that emerged after the introduction of cable, but now on a massive scale.
So, if cable and TiVo are any indication, viewers will move down the tail when supply is available. As broadband comes online, the tail gets infinitely long, and the curve will flatten our a bit, furthering gains for the mid-tail at the continuing expense of the head.
And there lies the problem. TV advertisers tend to be brand advertisers, and the value of TV advertising is as much about reach as it is about show brand affiliation. How does an advertiser (media buyer) pick from an infinite number of shows? How do they even begin to move down the tail, even moderately?

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