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 ability to do cool hacks on language level. I don't consider tabs as a crime against nature.
Which one is closer to LISP: Python or Ruby? 
I can't seem to be able to choose from Python and Ruby: they seem very similar but apparently Ruby is more functional and object-oriented, which are good things, while Python is more like Perl: a simple scripting language. Do I have the right impression?
PS - This might seem like a flame bait but it's not really, I'm just trying not to go crazy from OCD about switching from RoR to Python/Django and back.
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.
Please advise on Ruby vs Python, for someone who likes LISP a lot