It probably started with HTML, and then Yahoo, of course. But eBay escalated the hatred and Google and Facebook have institutionalized it.
To have lame typography, to avoid opportunities to speak not just with what you say, but how the letters look—this is part of the web's engineering-first ethos.
Sergey Brin famously said that marketing is the cost you pay for lousy products, and apparently, typography is a variety of marketing.
Sergey’s wrong about marketing, of course (great products are marketing), but doubly wrong about the benefits of typography.
Typography is what sets Apple, at first glance, apart from just about everyone at the mall. Typography is what makes a self-published book often look pale in comparison to a ‘real’ one. Typography (or the lack thereof) is a safety hazard on airplanes (who decided that all the safety labels should be in ALL CAPS)?
The choice of a typeface, the care given to kerning and to readability—it all sends a powerful signal. When your business card is nothing but Arial on a piece of cardboard, you’ve just told people how they ought to think about you… precisely the opposite of what you were trying to do when you made the card in the first place.
The irony here is clear. It was computer technology (particularly Apple) that put typography into the hands of all of us. And it’s computer technology that is relentlessly picking it apart, devaluing expression in a misguided attempt to demonstrate that you’re too busy coding to make anything look trustworthy or delightful. Typekit and other web solutions are trying to address this problem, and it's pretty clear that the next generation of sophisticated organizations online is going to look a lot better than this one does.