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Ruby on Rails Mac OS X - Leopard
Since Mac 10.5 Leopard, Apple has been shipped with Ruby on Rails! Ruby on Rails is an MVC framework that lets you scaffold applications together in minutes. It's very quick.
Here's a great tutorial that will get you started:
http://developer.apple.com/tools/developonrailsleopard.html
To get the most out of this you should be familiar with MVC (Model, View, Controller), and understand the concepts of functional and unit testing. To follow the tutorial to the letter, you'll need Xcode which is Apple's free IDE for building Mac OS X Applications. You'll want this IDE if you're interested in iPhone Applications too. How can so much good stuff be free? Easy: It's not Microsoft!
You might also be interesting in this interactive tutorial on Ruby: http://tryruby.hobix.com/. Just type "help" into the active window to start the Ruby Tutorial. In your console, you can also install an Interactive Ruby Shell (known as "irb") like so: sudo apt-get install irb. This is often a good way to practice.
Check out these books too:
Programming Ruby: The Pragmatic Programmers' Guide, Second Edition
http://www.amazon.com/gp/product/0974514055
Agile Web Development with Rails, 2nd Edition
http://www.amazon.com/gp/product/0977616630
And for a complete list of Ruby on Rails Tutorials
http://railsforum.com/viewtopic.php?id=6790
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