You say "both languages are just a mess" as if to equate the two. But there's no comparison.
Your Ruby problem with blocks and Proc objects is a nit about elegance and semantics. How often does the difference between an actual Proc object and a block actually affect you? More importantly, if the cost of fixing that nit is that we wind up with Lisp's or Javascript's lambda notation, who would accept that? Javascript has relatively consistent semantics for anonymous functions, but extremely clumsy syntax.
Python simply doesn't have real lambdas. It has the ability to pass something called a lambda in place of a function, and that something forces you to think about things like the difference between a statement and an expression. It then tells you that you don't in fact want anonymous functions, but instead you want to define tens of itty bitty named functions and use them instead. You also "want" that "self" argument to all your methods, and you "want" to tack two underscores to the front of your method names to make them private.
So, I half agree with you. Yes, it would be nice if there was a (zero-cost) way of fixing Ruby's block semantics. Yes, I can rely on Lisp's lambda semantics slightly more than I can on Ruby's, which does start to matter when you start writing domain-specific language code. But I don't agree that this has any bearing on the Python vs. Ruby argument. Python lambdas suck.