Ruby 1.8.6 is fully supported in Mac OS X Leopard including Ruby on Rails, Mongrel, Capistrano, and many other popular Ruby gems (packages). For details, see the Ruby wiki at MacOS Forge.
Mac OS X Tiger is packaged with version 1.8.2 of Ruby, but, for those who haven’t upgraded to Leopard, there are a number of options for installing the latest version of Ruby. Locomotive is a nice choice if you are looking for something to get you up and running quickly for Rails development. Using MacPorts or Fink might be a little nicer for the more technically savvy.
On MacPorts, you can install Ruby with…
% port install ruby
Fink has a graphical interface (using Fink Commander) for installing Ruby.
Also, since OS X is based on Unix, downloading and installing from the source is just as easy and effective as the other solutions.
For a detailed look at installing Ruby (and Rails), Dan Benjamin’s excellent article Building Ruby, Rails, Subversion, Mongrel, and MySQL on Mac OS X will get you up and running very quickly.