Bert Williams

Bert Williams was, to put it mildly, a monumental talent. Born in Antigua, he came to the US as a child and eventually became one of the highest-paid entertainers of his time, proving that even in the deeply segregated world of Vaudeville, genius — especially genius willing to don blackface for mass appeal — could find a way.

His stage persona, "The Bahamian," was a masterclass in nuanced performance, allowing him to subtly subvert stereotypes even as he portrayed them. He was a comedian of the highest order, but also a serious actor and singer, whose work influenced generations of performers, both Black and white.

While he spent much of his career performing in blackface, a practice now seen as deeply problematic, it's crucial to remember the context. This was the only path to mainstream success for many Black performers of the era, and Williams used it to open doors and subtly elevate the discourse, becoming a Ziegfeld Follies headliner and recording artist. He may not have been Jewish, but he certainly knew a thing or two about performing under pressure and making the most of a tough crowd.