I love this theory that not having a decent debugger is somehow a good thing - here's Giles Burkett:

Asking why Ruby has weak debugger support is like asking why a dolphin doesn't have gills. Ruby has weak debugger support because Ruby programmers shouldn't be using a debugger. Ruby supports TDD and BDD better than any other language except possibly Smalltalk. Debugger support is for languages that you can't run tests against gracefully.

Yes, Smalltalk supports it better, in large measure because we have a debugger. For instance, have a look at this short (unnarrated) screencast. The summary: The Smalltalk debugger can support TDD:

So no Giles, the absence of a debugger is not a feature - it's a fairly significant lack in your toolset.

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