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Screencast for Pry, a Ruby REPL.
If you're using Pry with Rails, you'll want to check out this Railscast (railscasts.com/episodes/280-pry-with-rails). Among other things, it shows another way of loading your app with Pry.
Here is also discussion and expansion on the loading scheme I showed in the video (gist.github.com/941174).