Answer: When a politicial tries to speak to teens in their own language
Trust me on this, you can search and search, but you will never find a finer example of anti-cool. My favourite quote:
So, cut it with the bling bling and do something for the community, man. Join in and take action with any of the groovy sites we've listed, or just drop Tom a line for a quiet rap by the electronic e-mail. Tom's well-up on the Interwebnet, and he won't harsh your buzz or dis you down the line.
If this was a parody, it would be brilliant. Tragically it is not.
Update: I've been had
It is in fact a parody. I do feel suitably stupid.