From the early years, when he morphed from celebrated poet to provocative singer-songwriter, to his induction into the Rock and Roll Hall of Fame, Leonard Cohen has endured as one of the most enigmatic and profound figures—with a uniquely compelling voice and unparalleled depth of artistic vision—in all of popular music. The aesthetic quality and intellectual merit of Cohen’s work are above dispute; here, for the first time, a team of philosophers takes an in-depth look at its real significance. Want to know what Cohen and Kierkegaard have in common? Or whether Cohen rivals the great philosophical pessimist Schopenhauer? Then this book is for you. It provides the first thorough analysis of Cohen from various (philosophical) positions. It is intended not only for Cohen fans but also undergraduates in philosophy and other areas. It explores important neglected aspects of Cohen’s work without attempting to reduce them to academic tropes, yet nonetheless will also be useful to academics—or anyone—beguiled by the enigma that is Leonard Cohen.