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I would consider Java to be simpler, but i see this is subjective and C seems like a popular language to proceed with. In java most of functionality we need is available as standard library.

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Depends on the target. It would be much harder to implement Java with a assembly target and some of the standard library because you would have to implement that from scratch. Not only that, but you have to deal with vtables from inheritance and class layouts. C doesn't require any of that complexity.

That being said, I think it would be very valuable to see somebody implement at least a partial version of Java with standard library (such as generics or at least collections) with assembly as the target.

Sorry i did not completely understand your comment. You mean to say, to implement a subset of C. I have already answered that question. Before we implement a real language or a part of it, implementing mathematical expressions has to come in place with actual code. Reason is, before we jump to implementing an actual language, we can learn all the phases of a compiler, simply compiling expressions into assembly. Extrapolating, we can implement a subset of C, which is not easy to begin with, but with experience, it is achievable.

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