This dissertation explores an under-studied yet key aspect of Dubuffet’s figuration—the intersections between Surrealism, ethnography, and performance in his portraits of writers and artist-intellectuals seeking to transform art, culture, and the human image in the post-WWII context. As I argue, Dubuffet produced his portraits in dialogue with the writings of certain of his key sitters, whose prose extolled alternative art forms as a means to transform Western art and culture. Considering Dubuffet’s portraits in relation to his and his sitters’ writings, as well as arts and ethnographic publications, I reveal his looking, for artistic inspiration, to the very cultural forms that had informed his sitters’ production. Many of these are Oceanic masks and figures found in Surrealist collections. Intriguingly, however, many are Indonesian masks, costumes, and puppets that have received scant attention in art historical studies. Combining a variety of visual sources to produce hybrid figures, Dubuffet aimed, I argue, to both affect the viewer and promote a thought-provoking artistic experience. In foregrounding the physicality of his figures in relation to the painting’s surface, moreover, Dubuffet calls attention to the very structure of the tableau, foregrounding the embodied and enculturated, experiences of the viewer. Chapter One, “Animat[ing] the Material:” Dissociation, Performance, and Ethnography in Dubuffet’s Portraits of Antonin Artaud, considers Dubuffet’s painting in relation to the mad Surrealist’s celebration of the affective qualities of Balinese stagecraft in his book The Theater and Its Double. Chapter Two, “The Hand Speaks:” Dislocation, Creativity, and Meaning in Dubuffet’s Portraits of Henri Michaux, considers these likenesses with regard to an aesthetic of displacement in Michaux’s book A Barbarian in Asia and to a variety of Indonesian masks and puppets. Chapter Three, “Evocations and References:” Assemblage, Translation, and Transformation in Dubuffet’s Portraits of Michel Tapié, considers Dubuffet’s depictions of this painter, critic, and curator in tandem with the Oceanic motifs to which, I argue, Dubuffet turned to produce his hybrid, collage-like figures. “Transmuting:” Collage, Theatricality, and Performativity in Dubuffet’s Self-Portraits, concludes the dissertation with an overview of Dubuffet’s career-long engagement with hybridity, collage, and performativity gleaned through his self-portraiture.