@Zorkerman
I have experience with both Jython and JRuby... a lot more with JRuby.
I must say they are great platforms, and you get the huge benefit of dynamic languages, PLUS the rich 3rd and 1st party library support of Java, PLUS a highly platform independent base compiled language, PLUS garbage collection in both languages (it's important to understand memory management, but I'm of the camp that you are better off avoiding it unless you REALLY need it, such as if you are doing drivers or kernel level stuff, or stuff that need every ounce of performance you can muster).
I just want to give a quick anecdote. I recently was building a ruby script to index a Solr instance, and I needed to access a DB2 database (the source of our data to be indexed). Straight Ruby failed miserably... it has horrible DB2 support, which requires a full install of DB2 express edition... which still didn't work as advertised (I couldn't compile the Ruby drivers after I had finished installation). The solution was to just switch to JRuby and use JDBC from the Ruby side, using a couple easy to install jars (and much much MUCH smaller files than the DB2 install).
I would definitely highly advise considering JRuby or Jython instead of using C as your back end... I've found that algorithm and resource performance usually have a much much bigger impact on application performance than the language you pick, and the Java platform has so much to offer (and it has come a long way since the early days when people were decrying it as vastly slower than C/C++). Unless you are doing very heavy calculation intensive things that can't be refactored algorithmically, you most likely won't need to drop down to the compiled language, regardless of your pick.
PS The integration with Java in JRuby is very seamless (from the JRuby to Java side anyways), so maintaining a bridge is not an issue. Jython I think is the same, but again my experience with it is a lot less.