I think we can start to see a pattern emerging here. Drupal gets nominated for a Webware 100 award and goes on to win yet again in 2009.
I won't go on at length about this, but its worth mentioning that Drupal's peers in the award category included Facebook, MySpace and Twitter. The majority of people out there still don't use Drupal and Facebook in the same sentence, but with more wins like this it won't be long until Drupal is universally recognized.
Congrats to all the hard work of core and contributed module maintainers and all the documentation writers and all the admins, bloggers and general supporters that make Drupal so great.