There isn't really a lot to separate Python and Ruby. I'd say the Python community is larger and more mature than the Ruby community, and that's really important for me. Ruby is a more flexible language, which has positive and negative repercussions. However, I'm sure there will be plenty of people to go into detail on both these languages, so I'll throw a third option into the ring. How about JavaScript?
JavaScript was originally designed to be Scheme for the web, and it's prototype-based, which is an advantage over Python and Ruby as far as multi-paradigm and metaprogramming is concerned. The syntax isn't as nice as the other two, but it is probably the most widely deployed language in existence, and performance is getting better every day.
