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This chapter discusses the taxonomy of imaginary literary works (supplementing the taxonomy of fictionalized life‐writings proposed in Chapter 5), and their scarcity during the nineteenth century. It concludes the discussion of Joyce, and ends with an account of Stein's Autobiography of Alice B. Toklas as an indisputable example of a fictionally authored auto/biography.

Gertrude Stein proposes an expansive and novel aesthetic theory of meaning’s autonomy by pointedly refusing normal punctuation in Lectures in America (1935) and Tender Buttons (1914). She rejects punctuation to keep the reader’s breath out of the text, just as, she argues, the frame of a landscape painting keeps out the air of the spectator’s world. Unlike New Critical or Frankfurt School accounts of autonomy, Stein’s also instantiates her support for universal suffrage: telling the reader when to breathe is understood as a violation of the reader’s political rights. Instead of producing an art that merges content and context—a poem and its reader’s particular space in the world—Stein respects both the text’s independence and the reader’s privacy by declaring everything specific to the reader irrelevant to her art.

This chapter suggests that the poetics of T. S. Eliot and Gertrude Stein may be seen as two sides of the same coin. It begins by examining that coin itself, which is the Modernist aesthetic, shared by Eliot and Stein, even as it was shared by Pound and Joyce, and the other central figures of the period.

This chapter cross-reads Picasso’s paintings that reference Stein—Gertrude Stein (1906), Homage à Gertrude (1909), and The Architect’s Table (1912)—with her word-portraits “Picasso” (1912) and “If I Told Him A Completed Portrait of Picasso” (1924) to argue that masculine homosociality was an important force in their dynamic. Tracking the ways their portraits of one another use cubist strategies to register the vicissitudes of their bond, I argue that whereas Picasso’s portrait of Stein reflects his trepidation about her masculinity and their masculine homosociality, her portraits of him instead show both fondness and concern about his uneven patterns of artistic production and imperial masculinity. If ultimately, Stein’s portraits of Picasso differentiate her queer transmasculinity from his misogynist masculinity, Czech artist Jiří Kolář’s reinflections of his portraits of her further transform the gaze through which her masculinity—and homosocial bond with Picasso—are made available for view.

This chapter examines Stein’s friendship with Ernest Hemingway, whose initial supplication to her tutelage transformed into aggression in the wake of his observation of Toklas’s power over Stein. Whereas Stein admits in The Autobiography to having “a weakness for Hemingway”, Hemingway—who spoke of wanting to “lay” Stein—spitefully attacked her relationship with Toklas in A Moveable Feast in retaliation for her calling him “yellow.” Differences between the public and private Hemingway precipitated crises as he disavowed the possibility that his attraction to the masculine Stein may have been driven by a far queerer configuration of gender and desire than the heteronormative logics that governed the works he published during his lifetime. Considering A Moveable Feast as well as Stein’s and Hemingway’s shorter poems about one another—Stein’s “He and They, Hemingway” (1923), “Evidence” (1929), “Genuine Creative Ability” (1930), and “Sentences and Paragraphs” (1931); Hemingway’s “The Soul of Spain” (1924)—this chapter argues that their relationship’s troubling vicissitudes reverberated across their lives and works.

This chapter presents literary modernism as a matrix of coterminous and varied movements that experimented radically with narrative form by reconfiguring linguistic systems of expression and signification. These strands of modernism led authors to fashion new literary idioms that could better evoke the irreducible multiplicity of actual U.S. speech forms, which made a singular American language inconceivable. This chapter poses a contrast between two of the most audaciously ambitious, linguistically innovative modernist novelists: Gertrude Stein and John Dos Passos. Stein's The Making of Americans opens up wholly unexpected possibilities of early modernist linguistic and literary utopianism. Teetering on the edge of coherence, the Making confronted the logic of efficient, functionalist language with her flaunting of aural vernacularity unmoored from narrative and mimesis. Dos Passos's sweeping U.S.A. indicated another kind of ambition for modernist language and narrative, comprehensive inclusivity of all of the languages and accents of the national populace. Yet, Dos Passos's Depression‐era, late modernist suspicions of leftist politics and narrative experimentation led him to turn his trilogy into a dystopic elegy of the failure of grand ambitions to rearticulate the nation and transnational modernity itself through newly inclusive literary idioms.

The Introduction provides an overview of Gertrude Stein’s Transmasculinity as well as a theoretical framework for understanding the relationship between Stein’s writings and her gender. By using psychoanalysis to complicate historicist imperatives and engaging recent debates over queer temporalities and relationalities, the Introduction lays the groundwork for the book’s argument that Stein ultimately rejected early twentieth-century gender formations in favor of a flexible, feminist, and anti-identitarian mode of transsubjectivity inscribed in texts that cross genres. Pushing back against formalist and materialist critiques of biographical interpretation, the Introduction also makes the case for readings that trace visual artworks’ and her writings’ roles as nodal points for intersubjective desire. The Introduction concludes with an overview of the book’s seven chapters and coda: four chapters that identify signs of Stein’s transmasculinity in her writings and others’ representations of her; three that track her masculine homosocial bonds with Pablo Picasso, Ernest Hemingway, and Carl Van Vechten; and a coda that points to possibilities for examining the implications of Stein’s masculine homosocial bonds with Vichy collaborator Bernard Fäy.

This introductory chapter discusses the beginnings of the friendship between two intellectuals, Gertrude Stein and Bernard Faÿ, which served as the context for reconciling Stein's “progressive” experimental writing and her later “reactionary” politics. Both Stein and Faÿ would find that they had many things in common, yet perhaps the most profound—if not the most troubling—aspect of this friendship was their mutual admiration of Philippe Pétain, whose politics seemed counter to Stein's progressive, avant-garde aesthetics and beliefs. Further complicating the issue wasthe troubled backdrop of the interwar years—wherein the political upheavals following the First World War had given way to jadedness for the current political systems, as well as the formation of new hybrid political movements—with an uneasy Europe struggling to come to terms with the United States' siren's call for “modernization.”

This chapter focuses on the unique wartime experience of Stein, an experience that was spent apart from Bernard Faÿ and that would ultimately distance her from Faÿ. With the French–German armistice in June 1940, the Stein–Faÿ collaboration of the 1930s—an intellectual, artistic, and emotional collaboration characterized by genuine affection and mutual political conviction, as well as desire, ambition, and egoism—was transformed into a collaboration of each with the Vichy regime. During this period, Stein and Faÿ had little contact with each other; after World War II they would never see each other again. Yet this experience was in fact marked by the invisible hand of Bernard Faÿ.

This chapter offers a counterpoint to Stein’s and Hemingway’s mutual aggression by focusing on her queerly productive friendship with modernist impresario Carl Van Vechten. Van Vechten’s friendship with Stein and Toklas was flirtatious and never soured. Rather than deriding Stein’s writing—as Hemingway and Picasso occasionally did—Van Vechten helped place her manuscripts, edited her Selected Writings, organized her 1934-1935 lecture tour of the United States, and took photographs that furthered her celebrity image. To track the vicissitudes of their bond, this chapter reads Stein’s temporally warped account in The Autobiography of her first meeting with Van Vechten; examines her two word-portraits of him (“One Carl Van Vechten,” 1913, and “Van Or Twenty Years After,” 1923); and analyzes several of his photographs of her and the “Woojums” family of choice they formed with Toklas. In a circuit of masculine homosocial desire that was markedly different than those addressed in chapters Five and Six, Stein returned Van Vechten’s affection with verbal portraits that show none of the ambivalence at work in her writings about Picasso and Hemingway.

This chapter uses The Autobiography of Alice B. Toklas to frame and advance this book’s central argument about Stein’s masculine homosocial relationships with her colleagues. Tracking the dynamics of vision that animate The Autobiography, I argue that it uses Toklas’s loving gaze to establish and recognize Stein’s masculinity, as well as to highlight the importance to modernism of her masculine homosocial bonds. The Autobiography depicts those ties as very congenial with men such as Sherwood Anderson and with masculine women such as Jane Heap, but more fraught—and more likely to induce perspectival vacillation—with Hemingway and Picasso. This multiperspectivalism structures the book and mobilizes multiple narratives of modernism’s emergence. In so doing, The Autobiography reframes Stein’s masculinity and relationship with Toklas as part of the appearance of the new that the text initially attributes solely to the formal properties of modern art and writing.

This chapter explores how Gertrude Stein draws upon her mentor William James’s ideas about habit, and how habit becomes central to Stein’s late World War II writings. James—like his counterpart Henri Bergson—celebrates habit as a mode of choice, and the strongest indication of a fully formed character. Similarly Stein locates habit—rather than innovation—as the most animating force in the English literary tradition. Stein inherits James’s positivism and understands habit as the pleasure of repetition. The value she finds in habit stands out against a dominating ethos against it, best articulated by Walter Pater, one of literary modernism’s key precursors. Stein’s emphasis on habit throughout her ouevre—both stylistic and ideological—becomes central to Mrs. Reynolds and Wars I Have Seen, texts largely based on Stein’s own experience during the German occupation of France. Habits both mask the disruption that war creates, dissolving the consequences of the world into the space of the home, and paradoxically work as a way in which war itself can be best represented. Stein’s World War II writings foreground habit’s crucial utility, but ultimately (and in contrast to Beckett) they also call attention to habit’s political inadequacy.

This is the first of two chapters that examine ways Stein’s increasingly experimental writings during the first three decades of the twentieth century gradually work through dominant early twentieth-century genders, loosening up and ultimately rejecting the rigid constructs of masculinity she encountered in Otto Weininger’s misogynist Sex and Character. Chapter Two focuses on cross-gendered identification in Stein’s earliest literary efforts—the prose narratives Fernhurst (1904-5), Q.E.D. (1903), and Three Lives (1909). In these works, Stein rejects the category “woman” while questioning the limitations of patriarchal ideologies about masculinity and femininity alike.

This chapter investigates how Gertrude Stein plays with the Künstlerroman. In The Autobiography of Alice B. Toklas (1933), she offers her own assessment of the position of the artist in a saturated media marketplace. Reading The Autobiography alongside Stein's other work, the chapter examines Stein's deployment of photographic illustrations, tropes, and techniques as a crucial strategy in her attempt to picture the history of modernism and to secure her spot within it. In particular, The Autobiography's underexamined photographs show how an ostensibly formless form—the surface—becomes the instrument of Stein's experimental history, as she skims across major developments in modernist and avant-garde art and literature and touches on as many famous figures as possible. In this way, while earlier chapters discuss the forms that populate modernist texts or the formal theories that purport to elucidate them, the chapter turns to the forms taken by modernism itself, which takes shape in the “contact zone” of The Autobiography.

This chapter examines Gertrude Stein and Virgil Thomson's opera Four Saints in Three Acts. It suggests that this opera was a landmark collaborative creation of U.S. modernist artists engaged in early-twentieth-century efforts to establish a distinctly and genuinely American voice in transatlantic high culture. It also highlights the queer expressive potential of artistic abstraction within the homophobic context of twentieth-century U.S. culture, and the crucial confluence of queer lives and culture with artistic activity and culture.

This chapter examines how and whether Gertrude Stein gives pleasure. Focusing on Stein's experimental writing from 1914 to her lectures of the mid-1930s, it suggests a new model for approaching her work: tickling. It considers tickling as an enduring social and scientific mystery and how its patterns illuminate Stein's methods and her reading effects. It also explores the ways that the gesture of tickling describes both the delights and difficulties of Stein's texts and also accounts for the wide discrepancies in readers' responses to her writing. Tickling, whose mysterious idiosyncrasies have intrigued theorists from Plato to Adam Phillips, characterizes Stein's infantile and erotic impulses, her abstraction and sensuality, and the sliding scale of pleasure to irritation that her work arouses. Stein's texts can be a pleasure machine or a torture machine or both, depending on the reader.

Chapter Two considers Stein’s literary treatments of pragmatist habit: her writerly experiments with punctuation, syntax, grammar, cliché, and repetition. The chapter argues that habit informs Stein’s modernism both formally and philosophically. In Stein, habit is at once a discursive structure and a subject of inquiry. Habit links Stein’s repetitions, perhaps her most characteristic literary mannerism, to her treatment of questions of national and institutional identity, literary history, and the intimate domestic routines she refers to as “daily island living.” Her literary experiments relate the minutiae of daily life to textual habits such as punctuation, syntax, and cliché, and to the collective habits of thought that create institutions, literary canons, and national identities. Stein takes as one of her most serious engagements the duty of rendering habit visible, and her literary materializations of the problem of habit make her one of our most striking, and unexpected, theorists and practitioners of pragmatic modernism.

“Seeing Stein’s Masculinity” analyses the shifting significance of visual images of and written texts about Stein. Driven by recent reinterpretations of Jacques Lacan’s theory of the gaze, this chapter reads his theories against the grain to counter arguments about the visual that reproduce binary thinking about gender. Queering his account of the gaze makes it possible to register the expanded array of masculinities mobilized in photographs of Stein by George Platt Lynes, Henri Manuel, and Man Ray as well as in their recent reception during the 2011 Seeing Gertrude Stein exhibit in San Francisco. Moreover, Stein’s own comments in The Autobiography about being photographed by Man Ray queer the heteronormative gaze that drives James Agee’s review of that book in the September 11, 1933 issue of Time whose cover featured Lynes’s image of Stein in profile. Tracking changes that have taken place between the early twentieth century and the present in attitudes toward her queer sexuality and masculinity, this chapter argues that traces of abjection remain in contemporary reactions to Stein despite greater acceptance of her gender, sexuality, and innovative writing.