Python is an experiment in how much freedom programmers need. Too much freedom and nobody can read another’s code; too little and expressiveness is endangered.
Ruby, on the other hand, is an experiment in “give every toddler a chainsaw”-level freedom. And as Gary says in that talk, you get some things like RSpec, ActiveRecord and Cucumber that simply aren’t possible at the lower “reasonable” levels of freedom.
95% of what only Rubyists can do with that freedom is horrible, irredeemable crap. But the other 5% couldn’t have happened in any other way.