Travis Jensen has an interesting post titled Our Dynamic Language Shootout:
For a variety of deployment reasons, we've decided that whatever we choose will be deployed on the JVM. As a result, this comparison is for the JVM versions of the languages, e.g. JRuby, Jython, and, of course, Groovy, which has no other deployment option. I want to also clarify that I have the most experience with Python and I really like the language. There is no doubt that the language influenced me in my evaluation, but I really tried to remain objective in spite of that.
As I did the evaluation, I tried to come up with a broad spectrum of important information. Others at my company gave feedback on the important characteristics. In the end, these are the features that we felt were most important: the interaction between Java and the selected language, the IDE support, the learning curve, existing web frameworks, and the existing community support for the JVM implementation of the language.
His conclusion: Groovy.
I don't think it should surprise you at this point that we chose Groovy. Even being openly biases towards Python first and Ruby second (hey, it's cooler :), I could not, in good conscience, choose either of them for melding into our existing environment.
If I were starting from scratch on a project, my choice would be very different. If I wanted to target the JVM, I would choose JRuby (at least until Jython 2.5 and Django are available); if I wasn't targeting the JVM, then it would be, for my Python, but I'd be equally comfortable choosing Ruby.
Well written Travis - I look forward to reading more about the new life you're breathing into your stilted development practices.