I am a C++ developer, slowly getting into web development. I like LISP a lot but don\'t like AllegroCL and web-frameworks available for LISP. I am looking for more freedom and a
Both Ruby and Python are fairly distant from the Lisp traditions of immutable data, programs as data, and macros. But Ruby is very nearly a clone of Smalltalk (and I hope will grow more like Smalltalk as the Perlish cruft is deprecated), and Smalltalk, like Lisp, is a language that takes one idea to extremes. Based on your desire to do cool hacks on the language level I'd go with Ruby, as it inherits a lot of the metaprogramming mindset from Smalltalk, and that mindset is connected to the Lisp tradition.