Gertrude Stein was an American writer, poet, feminist, playwright, and catalyst in the development of modern art and literature, who spent most of her life in France.

Early life
Born in Allegheny, Pennsylvania, a suburb later annexed by Pittsburgh, her Jewish-German family moved to Vienna and then Paris when she was three. After returning almost two years later, she was educated in California, graduating from Radcliffe College in 1897. She spent the summer of 1897 in Woods Hole, Massachusetts studying embryology at the Marine Biological Laboratory. This was followed by two years at Johns Hopkins Medical School.

In 1902 she moved to France during the height of artistic creativity gathering in Montparnasse. From 1903 to 1912 she lived in Paris with her brother Leo, who became an admired art critic. Stein met her life-long partner, Alice B. Toklas, in 1907; Alice moved in with Leo and Gertrude in 1909. During most of her life, Gertrude lived off a stipend from her father's estate, as did all of her siblings, which her brother Michael very capably stewarded and invested. After the success of her memoir "The Autobiography of Alice B. Toklas" in the mid 1930s, Stein became rich in her own right.

She and her brother compiled one of the first collections of Cubist and modern art. She owned early works of Pablo Picasso (who became a friend and painted her portrait), Henri Matisse, André Derain, Braque, and other young painters. Picasso also painted her nephew Allan Stein.

When Britain declared war on Germany in World War I, Stein and Toklas were visiting Alfred North Whitehead in England. They returned to France and, after Stein had been taught to drive by her friend William Edwards Cook, they volunteered to drive supplies to French hospitals; they were later honored by the French government for this work. Stein and Toklas became close friends with writer Natalie Barney, and Stein became friends with wealthy writer and magazine publisher Bryher.

By the 1920s her salon at 27 Rue de Fleurus, with walls covered by avant-garde paintings, attracted many of the great artists and writers including Ernest Hemingway, Thornton Wilder, Sherwood Anderson. She coined the term "Lost Generation" for some of these expatriate American writers. During this time she became friends (and some have speculated that they were occasional lovers) with writer Mina Loy, and the two would remain lifelong friends.

Extremely charming, eloquent, and cheerful, she had a large circle of friends and tirelessly promoted herself. Her judgments in literature and art were highly influential. She was Ernest Hemingway's mentor, and upon the birth of his son he asked her to be the godmother of his child. In the summer of 1931, Stein advised the young composer and writer Paul Bowles to go to Tangier, where she and Alice had vacationed, and he remained in that place which inspired his best work for the rest of his life.

Ernest Hemingway describes how Alice was Gertrude's 'wife' in that Stein rarely addressed his wife, and he treated Alice the same, leaving the two "wives" to chat. Alice was 4'11" tall, and Gertrude was 5'1" (Grahn 1989).

Politically, Gertrude Stein has been described as a conservative; she regarded the jobless as lazy, opposed Franklin D. Roosevelt and his New Deal. She advocated the Nationalist side during the Spanish Civil War. Judy Grahn (1989), in what is arguably an aggrandizement of Stein, describes her as "a 19th Century Republican; in her manners and manner of speech she was Victorian; socially was more liberal than not, with developed individualism coupled with democratic values based in pragmatism; thus at the opening of the German occupation of France she favored collaborative Vichy government, but by the end she did not, having witnessed firsthand the hardship it brought to the peasants."

World War II and after
With the outbreak of World War II, Stein and Toklas moved to a country home that they had rented for many years previously in Bilignin, Ain, in the Rhône-Alpes region. Referred to only as "Americans" by their neighbors, the Jewish Gertrude and Alice escaped persecution probably because of their friendship to Bernard Faÿ, a collaborator with the Vichy regime and connections to the Gestapo. When Bernard Faÿ was sentenced to hard labor for life after the war, Gertrude and Alice campaigned for his release. Several years later, Alice would contribute money to Faÿ's escape from prison.

After the war, Gertrude's status in Paris grew when she was visited by many young American soldiers. She died at the age of 72 from stomach cancer in Neuilly-sur-Seine on July 29, 1946, and was interred there in the Père Lachaise cemetery. In one account by Toklas, when Stein was being wheeled into the operating room for surgery on her stomach, she asked Toklas, "What is the answer?" When Toklas did not answer, Stein said, "In that case, what is the question?"

Stein named writer and photographer Carl Van Vechten as her literary executor, and he helped to usher into print works of hers which remained unpublished at the time of her death. A monument to Stein stands on the Upper Terrace of Bryant Park, New York.

Writings
After moving to Paris in 1903 she started to write in earnest: novels, plays, stories, libretti and poems. Increasingly, she developed her own highly idiosyncratic, playful, sometimes repetitive and sometimes humorous style. Typical quotes are

"Rose is a rose is a rose is a rose."

and

"Out of kindness comes redness and out of rudeness comes rapid same question, out of an eye comes research, out of selection comes painful cattle."

as well as

"The change of color is likely and a difference a very little difference is prepared. Sugar is not a vegetable."

These stream-of-consciousness experiments, rhythmical word-paintings or "portraits", were designed to evoke "the excitingness of pure being" and can be seen as an answer to Cubism in literature. Many of the experimental works such as Tender Buttons have since been interpreted by critics as a feminist reworking of patriarchal language. These works were loved by the avant-garde, but mainstream success initially remained elusive.

Judy Grahn lists the following principles behind Stein's work:

1. Commonality
2. Essence
3. Value
4. Grounding the Continuous present
5. Play
6. Transformation

Though she and her brother Leo collected cubist painters, the biggest visual or painterly influence on Stein's work is that of Cezanne, specifically in her idea of equality, what Judy Grahn calls commonality, distinguishing from universality or equality: "the whole field of the canvas is important." Rather than a figure/ground relationship, "Stein in her work with words used the entire text as a field in which every element mattered as much as any other." It is a subjective relationship that includes more than one viewpoint, to quote Stein: "The important thing is that you must have deep down as the deepest thing in you a sense of equality."

Grahn ascribes much of the repetition of Stein's work to her search for descriptions of the "bottom nature" of her characters, such as in The Making of Americans where even the narrator's essence is described through the repetition of narrative phrases such as "As I was saying" and "There will be now a history of her." Grahn: "Using the idea of everything belonging to a whole field and mattering equally, as well as each being having an essence of its own, she inevitably wrote patterns rather than linear sequences."

Grahn means value in the sense of overall lightness or darkness of a painting. Stein used many Anglo-Saxon words and few Latin-based words: blood instead of sanguine. She also avoided words with "too much association". "One consequence of developing value and essence as the basis of her work, rather than social themes, dramatic imagery or linear plots, is that she developed a remarkable objective voice. To an uncanny degree at times, social judgement is absent in her author's voice, as the reader is left the power to decide how to think and feel about the writing." Grahn continues, "Anxiety, fear and anger are not played upon, and this alone sets her apart from most modern authors. Her work is harmonic and integrative, not alienated; at the same time it is grounded useful, not wistful and fantastic."

Stein predominantly used the present tense, "ing", creating a continuous present in her work, which Grahn argues is a consequence of the previous principles, especially commonality and centeredness. Grahn describes play as the granting of autonomy and agency to the readers or audience, "rather than the emotional manipulation that is a characteristic of linear writing, Stein uses play." In addition Stein's work is funny, and multilayered, allowing a variety of interpretations and engagements. Lastly Grahn argues that one must "insterstand...engage with the work, to mix with it in an active engagement, rather than 'figuring it out.' Figure it in."

Though Stein influenced authors such as Ernest Hemingway and Richard Wright, as hinted above, her work has often been misunderstood. Composer Constant Lambert (1936) naively compares Stravinsky's choice of, "the drabbest and least significant phrases," in L'Histoire du Soldat to Gertrude Stein's in "Helen Furr and Georgine Skeene" (1922), specifically: "Everday they were gay there, they were regularly gay there everyday," of which he contends that the, "effect would be equally appreciated by someone with no knowledge of English whatsoever," apparently entirely missing the pun frequently employed by Stein.

Gertrude Stein wrote in long hand, typically about half an hour per day. Alice B. Toklas would collect the pages, type them up and deal with the publishing and was generally supportive while Leo Stein publicly criticized his sister's work. Indeed, Toklas founded the publisher "Plain Editions" to distribute Stein's work. Today, most manuscripts are kept in the Beinecke Library at Yale University.

In 1932, using an accessible style to accommodate the ordinary reading public, she wrote The Autobiography of Alice B. Toklas; the book would become her first best-seller. Despite the title, it was really her own autobiography. She described herself as extremely confident, one might even say arrogant, always convinced that she was a genius. She was disdainful of mundane tasks and Alice Toklas managed everyday affairs.

The style of the autobiography was quite similar to that of The Alice B. Toklas Cookbook, which was actually written by Alice and contains several unusual recipes such as one for Hashish Fudge (also called Alice B. Toklas brownies), submitted by Brion Gysin.

Several of Stein's writings have been set by composers, including Virgil Thomson's operas Four Saints in Three Acts, The Mother of Us All, and James Tenney's skillful if short setting of Rose is a rose is a rose is a rose as a canon dedicated to Philip Corner, beginning with "a" on an upbeat and continuing so that each repetition shuffles the words, eg. "a/rose is a rose/is a rose is/a rose is a/rose."