This work focuses on humanity's first technology—language—by placing the views of two of the greatest philosophers of the 20th century in direct confrontation on the topic of language/sign communication. It addresses the dominant role of language by the unexpected means of exposing the limits of words and signs for conveying meaning. Identifying these limits leads to the surprising realization that such limits are also precisely what make communication possible. Wittgenstein strives to shore up the foundation of meaning through a deeper understanding of the tension between rules and practice in the use of signs—while Derrida strives to expose the tension in the nature of the sign itself. This tension underscores the presence of the sign as intimately bound up with its absence. As a result, these two approaches feature contrasting roles for interpretation between a sign and its meaning. Highlighting the differences between these approaches reveals the play of hazards and benefits for language users when faced with alternative ways of understanding and accessing the power and potential of language.