1. Coverage. I don't know how he does it. He has minions scouring the net all day? He gets more Google News alerts than anyone? He spends all his day on his RSS reader? Whatever he does, he not only seems to get all of the relevant news on his site, he actually links to breaking stories faster than anyone else. Good reason to come back a few times a day, no?
2. Editorial. And by that, I am not referring to the right-leaning stories. I mean the mix of links he puts on his page. Obviously the top story is the biggest headline of the moment, but he goes beyond that. There is always an element of serendipity I enjoy when I go to his page. It's the equivalent of when a TV news casts blends in a story "on the lighter side" - or when you check into a news of the weird page. For instance, when checking the page today, I clicked on this story. Not essential news, but something that made my visit to Drudge entertaining - i.e. a reason to come back.
3. The Layout. Drudge, along with Craig, is the classic ugly but extremely functional design. In fact, 10 years later it is now part of his brand. Imagine if you saw a layout of his page but with the distinctive Drudge Report across the middle missing - you'd still know exactly where you were. His design is his brand - really a tough trick to pull off. My short list of folks who have done it include him, Craig and Google.
All of this leads to Drudge being a top 100 site year after year. Now, naysayers may argue that he got his "break" on the Monica Lewinsky story - or that he caters to a right wing audience. Both probably true. But, there are lots of sites that have their moment in the sun and then fade away and/ or cater to a specific audience. Not many stick around for as long as Drudge.
In an era where SEO and SEM decide where the traffic goes, Drudge has managed to succeed in publishing the old fashioned way: editorial, coverage, layout - and in the process, he managed to build himself a strong brand. I'm jealous.