The best approach still today to add scripting languages to your program is to go thru SWIG.
SWIG offers the ability to expose functions and classes thru a very minimal syntax and by reading C/C++ include files. Currently, it supports: Perl, Python, Ruby, Ocalm, TCL, and others. Code produced is usually very optimal and addresses many of the gotchas of each language, unlike something like boost.python which is a pig.
For exposing inheritance and similar, there is usually some more work involved in adding some custom wrapper code (and why something more automatic like CLR could indeed be a godsend), but it is usually rather painless.
CLR (and .NET) is indeed an interesting proposition which could indeed change the way we work…or be replaced or forgotten as so many other microsoft stuff of the past. I think the consensus is that the ideas are solid, but the implementation may still need some more polishing. Microsoft overall does not have a great reputation with languages and interfaces (COM, DCOM, Jscript, VB, etc.) and it is trying to regain a lot of ground lost to others (Java, python, web programming, etc). But it IS the best thing I’ve seen come out of MS in a long time. Albeit CLR is a microsoft standard, it was made freely open. Currently it still remains a windows only thing, albeit mono on linux is slowly making progress on supporting all of it and that could make it a more viable multiplatform paradigm. CLR takes some concepts from Java and others but improves on them (like allowing compiling to native code). The current new languages that supports CLR well, C# and VB.NET indeed shows its potential benefits (lighting fast execution equivalent to C++ when compiled to native code) and the drawbacks of CLR (garbage caching which is slower than references or having no memory management, no multiple inheritance and the CLR is considered not that good for supporting dynamic languages such as perl, python or ruby). The ability of interoperability of languages is possible, but under a certain set of restrictions described as CLS (ie. you may not be able to use some features of your favorite language if you expect the function to interoperate nicely with other CLR languages). Overall, CLR certainly seems like a much more interesting alternative than, say, Java and as mono becomes a solid framework on linux, and other nicer languages than those of microsoft appear, CLR could indeed catch on pretty fast. Of course, don’t expect to write something like a renderer with CLR. Applications where speed are a top priority will likely still remain in the realm of C/C++, but the type of applications where this is needed may become less and less with time.
Regarding wxRuby, forget it for now as the port only has a couple of months. Use rubyFOX, rubyFLTK which are very well supported (and, in my opinion, also better – assuming you don’t mind non-native widgets). Or you can use rubyTK, too, of course, if you are more traditional.