(Disclaimer: Not meant as flamebait)
Not to be a prick, but if you're having "typing" problems with Python, you're using it wrong.
Types are almost irrelevant in Python. What matters is whether, in a given situation, the method you're calling is supported and does what is intended. The actual type/class of the receiving object doesn't really matter, ditto for any arguments you pass to the method.
While this may seem highly unsafe and brittle, it has important benefits. You can just hack up some code that "just works" in a few minutes, without having to sacrifice a goat to the compiler first, making sure that all the correct types are specified, subclasses are defined, interfaces are implemented completely, etc. The rigid type systems in other languages often require this and more; making changes to your software becomes a chore. Rapid prototyping this is not.
In Python, when used correctly, you don't have this problem. Write a bit of code, write a test, run it, and decide what to do next. Ideal for testing out ideas. It doesn't work? Throw that shit out and write something else; two minutes later you'll be testing your new code again. Yes, you do need to have unit tests, but the same is (or should really be) true for most languages. Just because something compiles, doesn't mean that it does what you want. (Except maybe in Haskell. :-)
Interestingly, the quickly-written prototype might well be good enough to become the actual production code, with some additions. Just keep you tests up-to-date, for reasonable use cases, and there's no reason why your code shouldn't work in real life. Sure, that function foo(x) that wants to call x.bar() will fail if you call it with an x that doesn't support the bar() method. So don't do that, then! ;-)
Anyway, to summarize, I personally would much rather have Python's flexibility, paired with unit testing, than Java's lack of flexibility paired with compiler checks.