Bruce Eckel (author of amongst other popular books 'Thinking in Java') has doubts why anybody would switch from Python to Ruby. An interesting read: http://www.artima.com/weblogs/viewpost.jsp?thread=141312 To quote him: "The person I want to hear from is the core Python expert, someone who knows that language incredibly well, who has decided that Ruby is just so much better that all the mature Python libraries and community expertise doesn't hold a candle to the value of moving to Ruby. That person would be able to make a compelling, feature-by-feature argument" Any Python experts here? :)