Sherwood Anderson in his public introduction to Stein's 1922 publication of Geography and Plays wrote:
For me the work of Gertrude Stein consists in a rebuilding, an entirely new recasting of life, in the city of words. Here is one artist who has been able to accept ridicule, who has even forgone the privilege of writing the great American novel, uplifting our English speaking stage, and wearing the bays of the great poets to go live among the little housekeeping words, the swaggering bullying street-corner words, the honest working, money saving words and all the other forgotten and neglected citizens of the sacred and half forgotten city.
In a private letter to his brother Karl, Anderson said, "As for Stein, I do not think her too important. I do think she had an important thing to do, not for the public, but for the artist who happens to work with words as his material."
Other critics took a more negative view of Stein's work. F. W. Dupee (1990, p. IX) defines "Steinese" as "gnomic, repetitive, illogical, sparsely punctuated... a scandal and a delight, lending itself equally to derisory parody and fierce denunciation".
Composer Constant Lambert (1936) 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: "[E]veryday they were gay there, they were regularly gay there everyday." He writes that the "effect would be equally appreciated by someone with no knowledge of English whatsoever", apparently missing the pun frequently employed by Stein.
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. Stuart P. Sherman, however, refused to be numbered among those who stand in awe and admiration of one of the most eminent of the idiots, Gertrude Stein. He reviews her Geography and Plays in the August 11 issue of the Literary Review of the New York Evening Post and arrives at the conviction that it is a marvellous and painstaking achievement in setting down approximately 80,000 words which mean nothing at all.
Author Katherine Ann Porter provided her own estimation of Stein's literary legacy: "Wise or silly or nothing at all, down everything goes on the page with an air of everything being equal, unimportant in itself important because it happened to her and she was writing about it."
History Professor Blanche Wiesen Cook, has written of Stein: "She was not a radical feminist. She was Jewish and anti-Semitic, lesbian and contemptuous of women, ignorant about economics and hostile to socialism."
Writing for Vanity Fair magazine in 1923, eminent literary critic Edmund Wilson presciently came to an evaluation similar to the one made by Katharine Ann Porter some twenty years later, after Stein's death. Wilson deemed that Stein's technique was one of flawed methodology, using words analogous to the way Cubists manipulated abstract forms in their artworks. As Wilson wrote, unlike the plastic arts, literature deals with
- "human speech [which] is a tissue of ideas....Miss Stein no longer understands the conditions under which literary effects have to be produced...There is sometimes genuine music in the most baffling of her works, but there are rarely any communicated emotions."
An elevated observer, perched high above everything below, he likened Stein to a self-conceived "Buddha...registering impressions like some august seismograph".
Stein's literary output was a subject of amusement for her brother Leo Stein, who characterized her writing as an "abomination". Later detractors of Stein's work deemed her experimentation as the serendipitous result of her alleged inability to communicate through linguistic convention, deficient in the skills required "to deal effectively with language, so that she made her greatest weakness into her most remarkable strength".