Also, your Ruby vs. Python regex examples aren't even equivalent.
But on inheritance - you have to put the class name in round brackets in Python, no? That's 2 characters to Ruby's 1.
Stuff like a ||= shouldn't be considered Ruby-specific noise as Python also has the same idiom as in a += and a -=, just not with ||. || is arguably noise over "or" but it shouldn't seem like cryptic noise with any sort of experience of C, C++, Java, JavaScript, or almost any other mainstream language.
Further, that Ruby code of yours does seem more Perlish than Rubyish, but I suspect this is because Ruby style is gradually shifting away from Perl-like styles to more idiomatic approaches. For example, I'd probably choose 'string'[/re(g)ex/, 1] or if I was trying to be "proper" then something like m = string.match(/re(g)ex/); m[1] (or potentially use Regexp#match, but I far prefer String#match). I see those solutions more typically than those you present - and the latter is quite like your Python example - but.. TMTOWTDI and that's Ruby's greatest asset :)
also when i use regexps in ruby i then say "/re(g)ex/ =~ 'string' && $1". in python that would be multiple statements: "m = re.match('re(g)ex', 'string'); m.group(1)"
in python existing syntax (or more familiar syntax) is used to accomplish all the above.