This article explores the notion of interpretive difficulty in contemporary music, treating it as a structural, tangible aspect of analysis. Interpretive difficulty comprises any challenge a performer may encounter—physical, cognitive, emotional, specific to a musical passage, or generalized across a repertoire or performance idiom. Five professional performers who specialize in contemporary music are interviewed about their experiences learning and performing specific works—Crimson (Rebecca Saunders, 2005), Taurangi (Gillian Whitehead, 1999), Mani.Δίκη (Pierluigi Billone, 2012), Sept papillons (Kaija Saariaho, 2000), and La Nativité du Seigneur (Olivier Messiaen, 1935)—focusing on how interpretive difficulty and musical structure intersect in their practice. These interviews illuminate a relationship between interpretive difficulty and musical structure that manifests in several domains: accuracy, interpretive latitude, narrative, and control. While difficulty is uniquely determined by any musician's physical, cognitive, environmental, or cultural context, using these domains as a theoretical framework establishes relationships among works, performers, and idioms that might otherwise appear to have little in common—a particularly appealing prospect for recently composed repertoire. In subscribing to Nicholas Cook's (2013) recharacterization of the score as a “script” that is interpreted, supplemented, and molded in performance, this research encourages the treatment of performers' contributions as a fundamental object of analysis.