Paul Dooley’s composition, Masks and Machines (2015), is a significant new work for wind ensemble and was the winner of the National Band Association’s William D. Revelli Memorial Band Composition Contest award and the American Bandmasters Association’s Sousa/ABA/Ostwald Composition Contest. Masks and Machines has received positive critical acclaim and numerous performances, including a performance at the 2015 Midwest Band and Orchestra Clinic in Chicago, Illinois by the North Texas Wind Ensemble under the direction of Eugene Corporon and a performance at the 2016 American Bandmasters Association Conference in Lexington, Kentucky by the United States Marine Corps Band under the direction of Jason K. Fettig. The purposes of this dissertation are 1) to place Masks and Machines in its historical perspective within the history of wind band compositions; 2) to provide an overview of the artistic styles that influenced the composer, such as Stravinsky’s Neoclassical works, Bauhaus Art, and Fortspinnung; 3) to elaborate on the musical traits and characteristics of Masks and Machines via formal analysis; and 4) to offer a guide to rehearsal and performance of the work. The Introduction discusses Masks and Machines in its historical context as a highly acclaimed wind ensemble composition within the canon of twentieth century wind band works. Chapter 1 includes a detailed biography of Paul Dooley. Chapter 2 discusses the visual art and musical influences on Paul Dooley and how these influences come to life in his wind band compositions. Chapter 3 is an analysis of Masks and Machines with thematic excerpts and discussions on form, instrumentation, orchestration, and compositional techniques. Chapter 4 provides a rehearsal and performance guide aimed to facilitate a successful performance of Masks and Machines. Chapter 5 includes a transcription of two interviews with the composer and focuses primarily on compositional influences, processes, and techniques regarding Masks and Machines and other wind band compositions by Dooley, such as Point Blank (2012), Meditation at Lagunitas (2014), and Mavericks (2016).