Why PyROOT?
I discovered the Python bindings to ROOT in late 2004 and instantly preferred it to the awkward C++ interpreter. What I really like is that I can write a python script in one xterm and run it from another terminal with one line, which suits my usual debugging style. I also do almost all of my coding in Python these days - certainly I find input/output and string operations a breeze.
I also find the full-blown C++ interpreter to be just too much - if I want to write in c++, I'll write a c++ program. If I want an interactive shell I'll use bash. If I want something in between, I find Python's interpreter a lot more sane and quick than CINT. The implicit object-orientedness and garbage collection of Python makes working with ROOT in a script or shell much simpler - there's no need to use 'new' or worry about using '.' or '->'.