Some screencasts I'd like to see

I am particularly interested in the last item on his wish-list: Pry on Steroids: Interactive Ruby Development. Does anyone develop this way?

I'll admit that I am new to ruby and coming from Python I immediately fell in love with pry and was wondering if there was anyone out there who utilizes such a work-flow involving some sort of REPL. I have been having a hard-time figuring out a way to do this with pry in rails.