I think the problem is that the web still has little real mass-market coverage/awareness. I wouldn't even say someone like Danni Ashe or Drudge are someone that if I asked 10 people on the street, whether 1 or 2 might have heard of.

When the other media do look at the web, it's still seeing the web as a hodge-podge of novelties and personalities. And in most cases, this media is either directed at or consumed by "the converted" (people already in the loop.

The web is a wide-open space for anyone to do anything, but it's an amazingly closed world still, because it's still so unknown to those outside of it.

In addition, various elements of the web allow for a situation where one can get caught in (at least) two traps:

1) The time-warp: things don't always die on the web, they just sort of grow old and moldy making it virtually impossible for someone who logs on to the web today for the first time to know that Site X or Personality Y actually dates back to a phenomena of 3-4 years ago, rather than something new. So Site X and Personality Y will become "new" again and again to a new group of people with their popularity perhaps widening in scope but never really developing or growing in depth.

2) The self-referential loop: people tend to link to the same people who link to the same people and so people go 'round and 'round in this circle thinking that's as large as the web gets.