An interesting post from the dude that originally ported Python to the JVM and who just finished version 1.0 of the .NET Python port:
I started work on IronPython almost 3 years ago. My initial motivation for the project was to understand all of the reports that I read on the web claiming that the Common Language Runtime (CLR) was a terrible platform for Python and other dynamic languages. I was surprised to read these reports because I knew that the JVM was an acceptable platform for these languages. About 9 years ago I'd built an implementation of Python that ran on the JVM originally called JPython and later shortened to Jython. This implementation ran a little slower than the native C-based implementation of Python (CPython), but it was easily fast enough and stable enough for production use - testified to by the large number of Java projects that incorporate Jython today.
I wanted to understand how Microsoft could have screwed up so badly that the CLR was a worse platform for dynamic languages than the JVM. My plan was to take a couple of weeks to build a prototype implementation of Python on the CLR and then to use that work to write a short pithy article called, "Why the CLR is a terrible platform for dynamic languages". My plans quickly changed as I worked on the prototype, because I found that Python could run extremely well on the CLR - in many cases noticeably faster than the C-based implementation. For the standard pystone benchmark, IronPython on the CLR was about 1.7x faster than the C-based implementation...
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