You can garble filenames just as easily in statically-typed languages. Consider, for example, Windows' infamous 16-bit units that aren't actually well-formed UTF-16. I'm not aware of any widely-used programming language whose type system will save you from that sort of thing ("here's some bytes, figure out if they're a string and if so what encoding" is a historically very difficult problem).

You're getting downvoted because it's a flamewarish comment but as a mostly python dev, I think you have a point. Where types are so different that your code will throw a runtime error the first time you run it if you get typing wrong, you don't feel that much pain from dynamic languages. Also where types are being used like dicts explicitly as bags of stuff that might or might not be present/set, you can have the same thing in most typed langages with null errors. The place in my experience where a typesystem would have avoided some annoyance is where you have two very similar but not quite the same types that can fall a long way through your code before you notice. Str/Bytes is one, for me another common one is date/datetime. Fortunately in Python3 you can type annotate and just use a decorator to enfore runtime typechecks, this lets you track your assumptions and catch the errors closer to their origin.