Sure, maybe not the worst thing (I don't use Ruby primarily) but just one of the many things where the "expressiveness" of the language itself is can be as much

Sure, maybe not the worst thing (I don't use Ruby primarily) but just one of the many things where the "expressiveness" of the language itself is can be as much of a boon as it can be a nightmare. Misbehaving classloaders sounds like a straight up bug, or a lack of standardization around how a classloader should work. That doesn't sound so much like a failing of the language itself, but again, Java isn't my primary language so I'm not entirely privy to the landscape of Java fuckery. :)