Her career skyrocketed when she appeared at Harry Hansberry's Clam House, a well-known gay speakeasy in New York in the 1920s, as a black, lesbian, cross-dressing performer.

She dressed in men's clothes (including a signature tail coat and top hat), played piano, and sang her own raunchy lyrics to popular tunes of the day in a deep, growling voice while flirting with women in the audience.

On the decline of the Harlem speakeasies with the repeal of Prohibition, she relocated to southern California, where she was billed as "America's Greatest Sepia Piano Player" and the "Brown Bomber of Sophisticated Songs".

Bentley was openly lesbian early in her career, but during the McCarthy Era she started wearing dresses and married, claiming to have been "cured" by taking female hormones.

"[5] She believed that growing up feeling rejected shaped her behavior; she never wanted a man to touch her, hated her brothers, wore boys' clothes, and had a crush on one of her female teachers in elementary school.

She did not match the early-twentieth century beauty ideal of being slender and boyish, and she preferred to wear her brother's suits instead of dresses or blouses.

This is when she began performing in men's attire ("white full dress shirts, stiff collars, small bow ties, oxfords, short Eton jackets, and hair cut straight back"),[3] and here she perfected her act and became popular and successful.

[9] She toured the country, some destinations being Cleveland, Pittsburgh, Chicago, and Hollywood, where she was well liked by Cesar Romero, Hugh Herbert, Cary Grant, Barbara Stanwyck, and other celebrities.

[15]On the decline of the Harlem speakeasies with the repeal of Prohibition, she relocated to southern California, where she was billed as "America's Greatest Sepia Piano Player" and the "Brown Bomber of Sophisticated Songs".

As times progressed and federal laws continued to change, there became a point where Bentley had to carry special permits to allow her to perform in men's clothing.

Bentley was openly lesbian early in her career,[16] but during the McCarthy Era, she started wearing dresses and married (within five months of meeting) Charles Roberts, age 28, a cook, in a civil ceremony in Santa Barbara, California, in 1952.

In an effort to describe her supposed "cure" for homosexuality she wrote an essay, "I Am a Woman Again", for Ebony magazine in which she stated she had undergone an operation, which "helped change her life again".

The duo insisted that Bentley left them high and dry at the rise of the club and wanted to pursue other interests that she could financially benefit from.

[25] Fictional characters based on Bentley appeared in Carl Van Vechten's novel Parties, Clement Woods' novel Deep River, and Blair Niles' novel Strange Brother.

[26] In 2019, The New York Times newspaper began a series called "Overlooked No More," in which the editorial staff aims to correct a perceived bias in reporting by republishing obituaries for historical minorities and women.