Please, do check out the Pragmatic Studio (run by Mike and Nicole Clark). They have video courses on both Ruby and Ruby on Rails. The courses are well thopught-out, you can tell they put a lot of time and energy creating them. They take you step-by-step in a very didactic way from no knowledge of Rails or Ruby into applying intermediate concepts. Far from being just a Hello world application, but not confusingly difficult. They explain the core concepts really well and you have assignments for practicing what you've just learned.
These courses are not free though, but worth their price. My two cents.