My dad finds sites like Reddit/Digg/HN totally overwhelming, and I doubt he's alone. It's generational. Sites like NYT use standard design techniques to direct your attention (font size, etc) that work really well for people that are more-accustomed to traditional media. And, frankly, seeing a huge-headline is a much more-immediate way to indicate the importance of a topic than scanning down a list and looking for stories with lots of upvotes or comments.
The Drudge Report skews heavily for an older (50+) male demographic (going by Quantcast.) The design is text heavy, small fonts. A more static version of HN/Reddit, from one or two contributors rather than a community.
Funnily, I find digg/reddit/hn easy to skim, while NYT's front page layout is overwhelming to me (well, not easy to quickly skim for interesting content).
So I guess it depends on what you're used to. As usual.
