Born in Allegheny, Pennsylvania (now part of Pittsburgh), and raised in Oakland, California,[1] Stein moved to Paris in 1903, and made France her home for the remainder of her life.

She hosted a Paris salon, where the leading figures of modernism in literature and art, such as Pablo Picasso, Ernest Hemingway, F. Scott Fitzgerald, Sinclair Lewis, Ezra Pound, Sherwood Anderson and Henri Matisse, would meet.

(1903), about a lesbian romantic affair involving several of Stein's friends; Fernhurst, a fictional story about a love triangle; Three Lives (1905–06); The Making of Americans (1902–1911); and Tender Buttons (1914).

As a Jew living in Nazi-occupied France, Stein may have been able to sustain her lifestyle as an art collector, and indeed to ensure her physical safety, only through the protection of the powerful Vichy government official and Nazi collaborator Bernard Faÿ.

[14] After a year-long sojourn abroad, they returned to America in 1878, settling in Oakland, California, where her father became director of San Francisco's streetcar lines, the Market Street Railway.

[23] With James's supervision, Stein and another student, Leon Mendez Solomons, performed experiments on normal motor automatism, a phenomenon hypothesized to occur in people when their attention is divided between two simultaneous intelligent activities such as writing and speaking.

Writing of this period in her life (in Things As They Are, 1903) Stein often revealed herself as a depressed young woman dealing with a paternalistic culture, struggling to find her own identity, which she realized could not conform to the conventional female role.

In the lecture Stein maintained: average middle class woman [supported by] some male relative, a husband or father or brother,...[is] not worth her keep economically considered.

[27] From 1903 until 1914, when they dissolved their common household, Gertrude and her brother Leo shared living quarters near the Luxembourg Gardens on the Left Bank of Paris in a two-story apartment (with the adjacent studio) located on the interior courtyard at 27 rue de Fleurus, 6th arrondissement.

The art historian and collector Bernard Berenson hosted Gertrude and Leo in his English country house in 1902, facilitating their introduction to Paul Cézanne and the dealer Ambroise Vollard.

Dedicated attendees included Pablo Picasso, Ernest Hemingway, F. Scott Fitzgerald, Sinclair Lewis, Ezra Pound, Gavin Williamson, Thornton Wilder, Sherwood Anderson, Francis Cyril Rose, Bob Brown, René Crevel, Élisabeth de Gramont, Francis Picabia, Claribel Cone, Mildred Aldrich, Jane Peterson, Carl Van Vechten, Henri Matisse and Georges Braque.

For much of the war they sheltered in a house they had rented for several years in the hamlet of Bilignin in the commune of Belley (Ain), which was initially outside the area of direct German occupation in the Zone libre.

"[59] These stream-of-consciousness experiments, rhythmical essays or "portraits", were designed to evoke "the excitingness of pure being" and can be seen as literature's answer to visual art styles and forms such as Cubism, plasticity, and collage.

Stein predominantly used the present progressive tense, creating a continuous presence in her work, which Grahn argues is a consequence of the previous principles, especially commonality and centeredness.

[48] In addition, she wrote the first critical analysis of Stein's writing to appear in America, in "Speculations, or Post-Impressionists in Prose", published in a special March 1913 publication of Arts and Decoration.

[72] One of the earliest coming out stories,[73] it is about a romantic affair involving Stein and her friends Mabel Haynes, Grace Lounsbury and Mary Bookstaver, and occurred between 1897 and 1901 while she was studying at Johns Hopkins in Baltimore.

[74] In 1904, Stein began Fernhurst, a fictional account of a scandalous three-person romantic affair involving a dean (M. Carey Thomas), a faculty member from Bryn Mawr College (Mary Gwinn) and a Harvard graduate (Alfred Hodder).

The portrait of Madame Cézanne is one of the monumental examples of the artist's method, each exacting, carefully negotiated plane—from the suave reds of the armchair and the gray blues of the sitter's jacket to the vaguely figured wallpaper of the background—having been structured into existence, seeming to fix the subject for all eternity.

[93] Scholar Marjorie Perloff had said of Stein that "[u]nlike her contemporaries (Eliot, Pound, Moore), she does not give us an image, however fractured, of a carafe on a table; rather, she forces us to reconsider how language actually constructs the world we know.

[96][97] Published posthumously by Yale University Press in 1947, with an introduction by Thornton Wilder, Four in America creates alternative biographies of Ulysses S. Grant as a religious leader, Wilbur Wright as a painter, George Washington as a novelist, and Henry James as a military general.

In 1908, they summered in Fiesole, Italy, Toklas staying with Harriet Lane Levy, the companion of her trip from the United States, and her housemate until Alice moved in with Stein and Leo in 1910.

In an essay written at the time, Stein humorously discussed the complex efforts, involving much letter-writing and Victorian niceties, to extricate Levy from Toklas's living arrangements.

"[111] In the 1980s, a cabinet in the Yale University Beinecke Library, which had been locked for an indeterminate number of years, was opened and found to contain some 300 love letters written by Stein and Toklas.

That is what makes your identity not a thing that exists but something you do or do not remember.According to Janet Malcolm's contested account in Two Lives: Gertrude and Alice, Stein was a vocal critic of Franklin D. Roosevelt and the New Deal.

A compendium of source material confirms that Stein may have been able to save her life and sustain her lifestyle through the protection of powerful Vichy government official Bernard Faÿ.

Writing in the June 2005 edition of The New Yorker, Janet Malcolm describes: On July 27, 1946, Stein was operated on for what proved to be inoperable stomach cancer and died before coming out of anesthesia.

[141] Stein named writer and photographer Carl Van Vechten as her literary executor, and he helped to publish works of hers that remained unpublished at the time of her death.

[142] James Thurber wrote: Anyone who reads at all diversely during these bizarre 1920s cannot escape the conclusion that a number of crazy men and women are writing stuff which remarkably passes for important composition among certain persons who should know better.

[144] In his 1938 biographical novel The Green Fool, Irish poet Patrick Kavanagh describes the works of Gertrude Stein fondly as being "like whisky to me; her strange rhythms broke up the cliché formation of my thought".

[150] Stein was portrayed in the 2011 Woody Allen film Midnight in Paris by Kathy Bates, and by Tracee Chimo in the 2018 season of the television series Genius which focuses on the life and career of Pablo Picasso.