The thing with Drudgeretort.com is that it is just a knock off trying to attack the original. How often is the knock off as successful as the original. For those that would say that Google wasn't the first search engine, miss the point. Google created something different and better, Drudereport just tried to copy and paste their way to success, I however do think that Drudgeretort likely makes a descent bit of money, just not as much.
I however, do think that it is more the name, and the fact that he has always tried to show something different to the Main stream media that have lead to his success. He also knows his audience very well. I really don't think the design is the biggest element to his success, it is just a help to his success.
I hadn't visited the DrudgeReport in many years. The DrudgeRetort actually looks like (from what I remember) what the original used to look like. Interesting that www.drudge.com points to the retort, not to the original.