I never really got the "Worse is Better" essay. It obviously doesn't mean what everyone says it means and what it does mean isn't clear. This post points some of that out. For example, Worse in the essay was associated with simplicity. But the classic examples of Worse triumphing in the marketplace (the OP cites x86 as an example) are anything but simple: they are hypercomplex. Not only that, their complexity is largely what makes them Worse. Simplicity is rather obviously Better, not Worse. Smalltalk (which the OP cites as Better) is far simpler than its more successful peers. The more you look at the original essay, the more its conceptual oppositions seem muddled and at odds with history.
I've concluded that it boils down to exactly one thing: its title. "Worse is Better" is a catchy label that touches on something important about technology and markets and means different things to different people.
Such essays are always about concepts that cannot be precisely defined. That aside, I believe that it wasn't really simplicity that "worse" was associated with but easyness.
This distinction is well described by Rich Hickey (of Clojure fame) in his "simple made easy" talk. The key point is that simple-complex and easy-hard are two separate axes and that "easy" usually leads to "complex" (the case of x86, I believe) but you can invest some effort in shaping the environment so that "simple" can be "easy".
they are hypercomplex. Not only that, their complexity is largely what makes them Worse. Simplicity is rather obviously Better, not Worse. Smalltalk (which the OP cites as Better) is far simpler than its more successful peers.
It isn't about simpler it is about simpler for who. How is throwing away a million lines of C and starting from scratch in a language you have never used simpler than gently adding OO through C with classes? X86 and X64 maybe a terrible nightmare of complexity for somebody, but my apps keep working without change or recompile which is simplicity itself for me. Simplicity for you and simplicity for your customer are two entirely different things. C and Unix spread because it was capable of running everywhere and that provided real simplicity to the end customer(my software could run on lots of different hardware.)
x86 became hyper-complex, and won the market, because x86 chips have always remained backwards-compatible with previous x86 chips and software. Some issue as with Windows.
