A while ago I tried looking at how an object model for a Rake-tool would look like in Smalltalk. Here are the somewhat polished results of that experiment.

One area where Ruby fares definitely better than Smalltalk is in creating DSLs. This is mostly because of the "implied self" of Ruby's syntax, which however is also a major source of complication in parsing Ruby. Therefore, the Sake object model is also an experiment in using class extensions creatively to implement Smalltalk DSLs.