My answer would be neither. I know both languages, took a class on Ruby and been programming in python for several years. Lisp is good at metaprogramming due to the fact that its sole purpose is to transform lists, its own source code is just a list of tokens so metaprogramming is natural. The three languages I like best for this type of thing is Rebol, Forth and Factor. Rebol is a very strong dialecting language which takes code from its input stream, runs an expression against it and transforms it using rules written in the language. Very expressive and extremely good at dialecting. Factor and Forth are more or less completely divorced from syntax and you program them by defining and calling words. They are generally mostly written in their own language. You don't write applications in traditional sense, you extend the language by writing your own words to define your particular application. Factor can be especially nice as it has many features I have only seen in smalltalk for evaluating and working with source code. A really nice workspace, interactive documents, etc.