Ruby, hands down.
- Strong OO language. I believe it was partially based on smalltalk.
- The Object model is very well done, every thing is a first-class object.
- Meta-programming is easy to do
- has good support in IDEs like eclipse and RubyMine
- the gem library is huge and comprehensive - might be very close to CPAN and Python's.
- some good frameworks/tools/utilities out there like Ruby on Rails, Rake, scons, rdoc, etc
- some oddball, niche things out there too
- JRuby to write GUI applications. Runs on the JVM and has access to the JDK classes like Swing, AWT, etc.
Downside: the name. "ruby" means something to the outside world, expect google to bring you to jewelry stores, restaurants and Pokemon sites.
John