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.
- concise, simple language with little in the way of "grammar bling" (but check out http://chris-schmitz.com/ruby-question-marks-and-exclamation-points/  )
- some good frameworks/tools/utilities out there like Ruby on Rails, Rake, scons, rdoc, etc
- good community support (rubyforge.org)
- 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.
     - Ruby over JRuby on Android http://gonegoogling.com/2010/08/30/get-ready-to-ditch-java-creating-android-applications-with-ruby-using-ruboto/

Downside: the name. "ruby" means something to the outside world, expect google to bring you to jewelry stores, restaurants and Pokemon sites.

John