Bert Williams began performing to support himself through college at Stanford University⁵⁸. He met George Walker in San Francisco in 1893 and the two traveled east, billing themselves "Two Real Coons." In stark departure from Bob Cole and J. Rosamond Johnson who refused to wear blackface, the Williams and Walker team performed in blackface, rendering an indelible persona that would brand Williams for the rest of his professional life, and black theater for years to come⁵⁹. In Variety in 1907, the duo responded to the sharp critique of a professor, Albert Ross, who accused them of using ludicrous plantation stereotypes to entertain people. Williams and Walker responded to Ross's claim, explaining that dependence on white audiences forced them to bear in mind their expectations⁶⁰. After achieving unimaginable fame through their performance in Will Marion Cook's In Dahomey in 1902, the team would star in the hits Abyssinia (1906) and Bandana Land (1907). In 1910 Williams became the first black member of the Ziegfeld Follies⁶¹. With a chorus line of fifty women, all white, Williams' appearances would have to be limited according to the sex-race morays of the early twentieth century. Since he was not allowed to perform in scenes with white women, Williams appeared only in select scenes. He would be relegated to performing a comic monologue in his trademark style or to sing hard-luck ballads⁶². Black audiences were generally not admitted to the Roof Garden of a New York Theater where the Follies played in the summer, and were confined to the top sections of the theaters during the rest of the season. Williams remained with the Follies until 1918. After years of exclusion, Williams's frustration mounted. Theater historians Errol Hill and James Hatch note,

He did not eat or travel with the company; he had to find his own accommodations while on tour; use backroom elevators . . . having cast his lot with the all-white company he was unable to take an active part in the creative changes currently occurring in black theatre. Being a celebrated black actor whose skills were defined by wearing blackface was frustrating . . . To crown it all, the writers hired by Ziegfeld no longer produced interesting scripts or situations that Williams could develop⁶³.

Williams's exclusion from the company was typified in the company's treatment of him during a 1919 Actor's Equity Association strike:

I went to the theatre as usual, made-up and dressed. Then I came out of my dressing room and found the stage deserted and dark, the big auditorium empty and the strike on. I knew nothing of it: I had not been told. You see, I just didn't belong. So then I went back to my dressing room, washed up, dressed up, and went on the roof. It all seemed like a nightmare⁶⁴.

After leaving the Follies in 1918 he performed in Broadway Brevities of 1920 and Under the Bamboo Tree before his sudden death in 1922 at age forty-nine.