outdated : Some of these resources have shut down. I suggest signing up for the rubyrogues parlay mailing list for up-to-date discussion.
destroyallsoftware.com $9 for his entire back catalog. You can subscribe monthly or just sign up, download all of them and then cancel.
tryruby.org 15 minute ruby intro. Recently bought by the code school guys.
codeschool.com Has a free 2 hour rails tutorial called rails for zombies. This is really fun but longer. It’s totally interactive. Very well done. They have non-free classes too. Focuses on rails 3 and some advanced stuff.
railscasts.com Not very hand-hold-y. I regularly watch this site just to learn new things and watch someone work. These are short in length and very focused.
rubykoans.com Ruby Koans are practice exercises/meditations on different aspects of Ruby. There are many similar projects (Python Koans etc). It’s like an interactive cookbook. Very valuable to do even if you’re comfortable with Ruby. It’s a project that has failures built into it and it’s your job to fix them. I did a blog post on it. I’m not explaining this very well. It’s a bunch of tests set up to fail and you fix the first test case and it continues on. For example, you might set true = true and then the test suite will have 1 test passing and give you a progress bar. Very cool and easy to pick up and put down. Good for reference afterwards.
confreaks.net Lots of conference videos organized by events. The HTML5 player sucks. Use the flash one, even that one is a bit picky with pausing and other stuff.
quickie_mart 20 min app A plug! This is a talk that I did. The README is very short but has all the steps to build a store rails app. The repo is the completed app.