<p>Bill Wimsatt and Mark Wilson are each the author of a body of work whose fruitfulness is rivaled only by its forbiddingness. Despite deep sympathies between their approaches and conclusions, their work has not yet been read together. This paper makes the case for doing so. We identify a shared question at the heart of their work: how is it that limited beings such as ourselves come to possess genuine knowledge of a complex world? We then show that Wimsatt and Wilson arrive at similar answers to this question. Over a range of topics (investigative strategies, the uses of models, and theoretical and conceptual structure), both scholars emphasize the functional messiness of science. This is complemented by a pragmatist-leaning philosophical methodology that recognizes that one of the core uses of knowledge is to scaffold the acquisition of more knowledge. The core of the paper traces the mutually supportive interplay between their philosophical doctrines and methods. We end with two brief discussions: one a defense of their winding, playful writing styles, the other a brief consideration of the relationship between their work and Arthur Fine’s natural ontological attitude.</p>