Kahlil Gibran's artistic expression took two distinct and seemingly unrelated paths as he produced in parallel numerous symbolist paintings and a series of portraitures. The former survived in the illustrations of his seminal book The Prophet and a sundry of other publications, while Gibran's portraiture works have remained relatively unknown. Portraiture had always been Gibran's medium for connecting with people. Long before it became an artistic project, portraiture featured prominently in his courtship with the poet Josephine Preston Peabody, the young French teacher Emilie Michel, and his muse Mary Haskell. In his lifetime, Gibran was considered a talented portraitist to the elite of the cultural and social establishment. His subjects included Debussy, Rodin, W.B. Yeats, John Masefield, Sarah Bernhardt, Carl Jung and many other characters that populated the early part of the 20th century, and as such, this collection of portraits is a visual record of the cultural life of that period. The present work is the first systematic endeavor to assemble and assess this body of work, and offers a thorough exploration of the intersections of the lives of these individuals with Gibran's life.