Number 1: http://www.georgerrmartin.com
The esteemed place of number 1 web tragedy must go to George R. R. Martin. He's the man behind the HBO series Game of Thrones. In addition to his Song of Ice and Fire series the man has written a ton of novels and is a NYT #1 Bestselling Author. So why does his website look as if it was designed by a high school kid in the 1990's? Animated GIFs, bland graphics, and amateurish layout conspire to make this website a cartography of basic "web design don'ts".
It was "designed" by a "company" (and I use both terms in the broadest possible sense) named Mandala. A quick glance at their sites only strengthens my suspicion that they stay in business only by sub-contracting their web to teen LARPER's working from an old Sanyo using Paint Shop version 3.
Todd Fluhr is a freelance writer and multimedia designer. A self-described "Shockwave Rider" of technology, culture, and creativity, he has been involved in the interactive entertainment industry since the early 90's. He hopes to find time to sleep some day.