My guess for such sits: someone put a family member or friend in charge of the web site and no one has figured out a polite way to let the decider know what an idiot job it is. “Hey Ralph, your six year old nephew needs to be in therapy, not designing web sites.”
It’s the pro sites, like the recently redone weather channel’s local forecast pages that baffle me. (Go to Forecast - The Weather Channel | weather.com, type in a zip code and try to find basic info: forecast, current conditions, today’s high and low, etc., without having to click thru a half dozen pages.)
Cracked.com’s web design budget has been eaten up by massive bets in their in-house pool about whether they can use every available royalty-free photograph Getty offers before the end of the decade.
I’m mildly surprised that Ain’t It Cool news hasn’t done a redesign since the last time I went there, which was probably 1997.
Allmusic.com gets a little more boring and less useful with every redesign.
My pet theory about sites like the Weather Channel is that they’re really aggregators for advertising and sponsored content, and any useful stuff is simply the loss leader. So forcing you to click through a bunch of pages is supposed to expose you to ads and stuff that actually makes them money.
While not quite as bad as some others people have listed, philly.com deserves special mention. Keep in mind that this is the website for a major newspaper in a major city. Try taking a look at it without your adblocker. Also, try moving your mouse toward the beige horizontal bar right underneath the red bar up top. It’s damn near impossible to reach the buttons that say “opinion,” “neighbors,” “obituaries,” etc. without having dropdown menus from the adjacent red bar block your access.