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Gottleib Frege was a mathemetician working at a time when there was no rigorous definition of a number, which led him to conduct some groundbreaking work in linguistics. In his paper "On Sense and Referent" he proposed that words should be understood as having two sorts of meaning, similar (but not exactly the same as) connotation and denotation. His work had a profound impact on the work of Bertrand Russell.

Not long after, a school of philosophy emerged called logical positivism, which held (among other things) that the work of philosophy was to clarify terms of discourse for other disciplines. A.J. Ayer, in his (excellent but flawed) book "Language, Truth, and Logic" proposed a positivist program which asserted that metaphysical statements are nonsensical, and which admitted tautologies as the only sort of valid linguistic truths.

Around the same time as Ayer, Kurt Godel was working out his incompleteness theorem, which basically states that a formal system cannot be both self-consistent and able to express all truths about itself.

The ancient Greek philosopher Zeno proposed a Kafkaesque refutation of material existence: in order to go from point A to point B, one must first go half way; and in order to go half way, one must first travel half of that distance, and half the half distance, so on to infinity. So it's never really possible to go more than half way to any place (there's a more rigorous formulation of the problem involving a race between a Achilles and a tortoise). Zeno concluded that motion was impossible and the physical world self-contradictory. Because, however, he perceived things to exist, he decided his various perceptions of different things were acturally perceptions of a single cosmic substance; that is, we see different things, but really there is only one thing that just looks like different things.

In Plato's Parmenides, Zeno presents multiple arguments to a young Socrates in support of the position that "all is one," to which Socrates humorously replies: "So are you saying that there are fewer things in the universe than arguments you've just offered to demonstrate your point?"

Between these thinkers, we can see that words are limited and sometimes paradoxical, but that they nevertheless exhibit regularities in their irregularity which, if properly understood, can lead to greater understanding.