I've always been a pretty strong advocate of static typing, but my recent python programming experience has reminded me how much fun a dynamic language can be. Martin Folwer says as much in his entry on DynamicTyping:
Working with languages such as Java and C# I always feel the need to skip over text in order to understand what's going on. Whatever the reason, this better flow leads to more fun programming - even with an inferior environment. This may not seem to matter much, who cares if programmers have fun? But I do care because I really enjoy programming. I enjoy doing things quickly without having to futz around on guff that gets between my thinking and running code. For me that's the pleasure of Smalltalk and Ruby and why I reach for these on any personal projects. And there's business value in fun - after all motivation is a major factor in programmer productivity.
He does make a good point about static typing and the IDE that I've noticed. Eclipse is about the only thing I miss about python programming. I haven't tried out one of the python plugins. Maybe that would be the final nail in the coffin. I find myself thinking about using jythonc to compile to byte code.