The Rubygame gem includes the DLL file for Rubygame itself, but none of the libraries it uses. You must download this zip file of all the DLL files you'll need.
Visual Tutorial: Installing Rubygame on Windows
By Michael Morin, About.com Guide
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- Open a Command Prompt
- Install the Gem
- Select the Correct Gem Version
- Download the DLL Package
- Install the DLL Files
- Run the Program
- Obtain and Compile the DLL Files Yourself
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- Download the DLL Package