Ruby 1.8 brought us a couple changes that made many kinds of metaprogramming easier, plus a whole bunch of library additions that made Ruby feel more "grown up". Without seeking external libraries, one could write Ruby to solve many problems developers face in commonplace jobs. I wasn't around for Ruby 1.6, but I've been thinking of Ruby 1.8 as a transition from "better Perl or Java" to "better Smalltalk".
Ruby 1.9 brought us features that make some functional programming idioms easier. Lambdas, i.e. anonymous functions, require less syntax and are better defined. Enumerators make it possible to use features of Enumerable, itself a very functional-esque feature, in more places. Symbol-to-proc makes it easier to pass methods around as blocks, another FP-esque practice. I might say that Ruby 1.9 is the "better MatzLisp" version of Ruby.
Ruby 2.0 is bringing us features that, on the surface, make it easier for Rails to extend the Ruby language via ActiveSupport. I think that's too shallow of a reading. The new tools in Ruby 2.0 (excepting the highly-controversial refinements) make it easier to cleanly add functionality to Ruby's core objects and library. Reducing the cost of extending the core make it possible for more libraries and applications to judiciously make high-leverage additions to the lower levels of Ruby. That seems like a pretty good thing.
I can't find a source for this, but I could have sworn I once read that all programming is language design. It was probably related to Lisp, where you're arguably directly manipulating the AST much of the time. If the changes in Ruby 2.0 can take us closer to this level of program design, where we think more about building language up to the problem domain instead of objects and mechanism, sign me up.
