In contrast to monistic conceptions of hermeneutics as interpretation, legal hermeneutics has always been acutely aware of the complexity of our hermeneutic practices. The legal tradition thus speaks in favor a complex conception of hermeneutics that identifies the different activities involved. The chapter tries to show that such diverse activities as interpretation, rule-following, construction, association, the exercise of discretion, and judgments on significance can all be involved in the application of the law. All of these distinct practices involve distinct theoretical issues, most of which can be linked to particular debates in analytic philosophy. To prove the point that this complex conception of hermeneutics is not specific to the law, but applies to hermeneutics in general, some parallels in the field of the hermeneutics of art are drawn. In theoretically following up on the distinctions inherent in legal doctrine and methods, hermeneutics in general can live up to Gadamer’s observation that there is something to be learned from looking at the law.