I am a C++ developer, slowly getting into web development. I like LISP a lot but don\'t like AllegroCL and web-frameworks available for LISP. I am looking for more freedom and a
Alex Martelli gives a good analysis of the subject. It's a bit dated now, but I agree with the basic gist of it: Python and Ruby are two different ways of implementing the same thing. Sure there are some things you can do in Ruby that you can't do in Python. And sure Python's syntax is (arguably) better than Ruby's. But when you get down to it, there's not a whole lot of objective, scientific reason to prefer one over the other.
A common thing that you will hear is this: the platform is more important than the language and Python has a better platform than Ruby (this argument works both ways so don't vote me down, all you rubyists). And there is some truth to it. Unfortunately, it's not very relevant though. If you dislike the platform for either languages, there are implementations of both in Java and .Net, so you can use those if you have concerns about the platform.