Gertrude Stein has been the subject of many artistic works. Stein and Toklas merit their own line each in the song "Bosom Buddies" from the 1966 Broadway musical MAME, based on the stage play Auntie Mame, by composer-lyricist Jerry Herman. In MAME, Vera Charles, Mame Dennis' actress-confidante pal, sings: "...I'll always be Alice Toklas, if you'll be Gertrude Stein." (Bea Arthur who played the original Vera Charles on Broadway, recreated the same role for the 1974 film version of the musical.) In the 1998 Latin American literary classic "Yo-Yo Boing!", novelist Giannina Braschi pays homage to Stein as an imaginary mentor.
In 2005, playwright/actor Jade Esteban Estrada portrayed Stein in the solo musical ICONS: The Lesbian and Gay History of the World, Vol. 1 at Princeton University. "Loving Repeating" is a musical by Stephen Flaherty based on the writings of Gertrude Stein. Stein and Alice B. Toklas are both characters in the eight person show. Stein is a central character in Nick Bertozzi's 2007 graphic novel The Salon.
The posthumously-published Journals of Ayn Rand contain several highly hostile references to Gertrude Stein. From Rand's working notes for her novel The Fountainhead, it is clear that the character Lois Cook in that book was intended as a caricature of Stein.
Stein (played by Bernard Cribbins) and Toklas (played by Wilfrid Brambell) were depicted in the playful Swedish 1978 absurdist fiction film Picassos äventyr (The Adventures of Picasso) by director Tage Danielsson, with Gösta Ekman as Picasso.
Stein was also portrayed in the 2011 Woody Allen film Midnight in Paris by Kathy Bates. Her name is added to a list of great artists and notables in the popular Broadway musical "Rent" in the song "La Vie Boheme". Also mentioned in the Astaire - Rogers 1935 film Top Hat. She is mentioned in the song Roseability by the Scottish rock group Idlewild. Composer Ricky Ian Gordon's and librettist Royce Vavrek's opera 27 about Stein and Toklas premiered at Opera Theatre of St. Louis in June 2014 with Stephanie Blythe as Stein.