Why not Ruby?
I really don't care about the interviewing portion of the article. It's just that he's decided that Ruby is the Next Big Thing (basically because of RoR), and so his writing now reflects his need to make that happen:
Ruby is exceptionally easy to learn — far more so than Perl, C++, C#, Java, or even PHP. Oh hell, I’ll just say it: it’s easier to learn than Python ....
.... As it happens, Python is my second-favorite language ...
I really could defend all the points Steve goes into ... the whitespace thing, the "frosty" Python culture, the fact that Python people don't "get" marketing (probably the most accurate statement he makes). But there's really no need. You see, Ruby has all the same important things that are keeping it from widespread adoption that Python does.
A new programming language needs three things for widespread adoption: 1) accepted syntax (close enough to a C-like syntax that people feel comfortable), 2) good libraries, and 3) a good RAD IDE. The main problem is that Ruby has the first two items, but it doesn't have a good supporting IDE to go with it ... much the same as Python.
Java has Eclipse. C# has Visual Studio.NET. What does Ruby have? RADRails, which is in much the same position as all the other Python IDEs out there (Komodo, Wing, PyDev) ... it provides a sub-par experience compared to Eclipse or VS.NET.
I'm betting that I'm not far off in saying that Rails may even be Ruby's downfall. RoR may cause Ruby to be seen as a solely "web development" language, especially when its best IDE is tied to Rails.
Honestly, Python is much closer to breakout status at this point because of IronPython. Once IronPython gets fully integrated with VS.NET, its visibility will increase a thousand-fold. Plus, the third piece of the puzzle -- a killer GUI-builder/RAD IDE -- will be in place. It can't happen too soon.