Last year Jason Fried made a rather bold statement declaring the Drudge Report as one of the best designed sites on the web. I had recently been hired as a Designer, and I didn’t quite know what to think of this post. My boss explained to me (and 85,000+ people) that he thought the Drudge Report was one of the best designed sites on the web, and I disagreed with the statement.

It was only after launching the design for the 37signals site that I started to reflect back on the original sentiments of that Drudge Report post. Jason explained that the Drudge Report stands apart from the “news” pack. It is unique in its design—albeit plain—compared to the CSS mastery of other news sites. This simple and plain uniqueness actually makes it memorable.

It looks good, but what did it say?

We went through hundreds of designs for the Highrise, Basecamp, and 37signals marketing sites. I thought many of these designs were visually successful. Ultimately most were rejected on the basis of clarity. Each time Jason and I would have a design review he would inevitably ask, “What is this trying to say? Why is this important?” Then he would follow-up with the statement “Clarity above all else!” This would often result in making the font bigger, removing an illustration I spent hours on, or Jason rewriting complete pages of text.

It was during this time that I’d think about the sites that I appreciated from a design standpoint. Many of them are personal blogs or cool brochure sites. I began to realize that these sites displayed information well, but I could not exactly remember what they were about. They sure were pretty with fantastic CSS, but I can’t really remember what what the site said. Did it say anything?

I started to recall those amazing Flash Sites of the Day. You know those sites that get passed around via IM in your office on a slow day? Simply amazing design and programming. Problem is: I can’t for the life of me remember what those URLs were–much less the company/product that was being featured! Isn’t that the point with those sites? That the impact should be profound so that you remember Product or Company X?

And so it was in revisiting Jason’s Drudge-Report-Loving-Post that I finally began to understand: It doesn’t matter how awesome or slick the CSS or ActionScript on your site is. You have to make your site memorable. Your site has to speak clearly. Otherwise it may just end up as a web monument awaiting for another beautiful site to take its place.