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Let's start first by defining some aspects of the Web, and the people who use it.
The Web is a different medium than the mainstream media in several ways.
Power to the users (once named surfers): Users choose what they want to read on the Internet. On TV, although you can choose which channel to view, you are stuck with whatever you are presented with.
Interactivity: Not only is the web an interactive platform, it gives us the full range of choice between being totally passive, and just reading or viewing what's on there, and being totally active by logging in, writing, commenting, etc. We can also have any of the choices in between those two extremes. Even in the most passive of choices, you still have to click through to different pages to continue browsing, while on TV, you can just sit there till you sleep.
Person of the year 2006: More and more power is gained by the web, which is in its second version, and most Web 2.0 citizens want thier voices heard. The Web is emerging as an alternative underground tool where people who don't have access to huge mainstream media can find a way to express themselves and reach out to people.
The highly active users of the Internet are fed up with celebrities spamming thier lives, and looking for alternatives. They are also keen on becoming celebrities themselves. The long tail shows that there will be lots of small celebrities, who are enabled through Web 2.0 technologies.
The Web is for people who want to look for their own personal preferences. People who don't need to watch tonight's show just because everyone else is watching. Furthermore, it is for people who want to contribute, share, and make their voice heard.
Therefore, having a celebrity endorse a site or a web service might alienate these people. They want to be celebrities, not just see them. Mainstream celebrities are symbols of the media that these people are moving away from.
When might celebrities be useful?
When they are Internet celebrities: Of course! These celebrities can easily be identified with by the users, and they aspire to be like them in some way or another.
When online and offline merge: The line between mainstream and web applications and media is blurring, and this strategy might work for programs or channels that have both aspects to them. Luvoo is endorsed by Carmen Electra, and it is a TV show based on their matchmaking website.
I'll be checking this theory myself with a project I'm currently working on. Although I'm conviced that Internet users have the power to promote the people they think are popular, I will keep an eye on examples where this is and isn't working.
