So, I know this sounds crazy, but I feel like I am entirely right. But for some back story, I have been performing for years. I played piano and started writing music. Then, when I was a teen, the only places where a young black man could perform were in minstrel shows. The minstrel shows in California were where I started performing small musical numbers and experimenting with the Sambo archetype, which is in blackface. In 1893, I was 19 and joined a minstrel troupe called the Martin Mastodon Minstrels, which was the first integrated minstrel troupe*.* This is where I met a very close friend, George Walker. We started a duo act where he was the "Dandy", to my "Sambo", and we called ourselves, "The Two Real Coons”. We moved on to these theatre circuits. In these shows, we had a small slot for our act among multiple others of all types. I think it was called Vaudeville, but that doesn't matter, lol.

Once we started doing these Vaudeville shows, we started to get some moderate success. Here is where we made the cakewalk famous. These two random guys, Victor Herbert and Glen MacDonaugh, scouted us. They were working on this new operetta work called "The Gold Bug" with Herbert on music and MacDonaugh on lyrics/book. Both Walker and I wanted to take our act to the next level. So we took on the project, and we finally opened in 1896 as a minstrel act within the operetta. The show was a total flop and only lasted for 8 performances. But our act turned out to be a massive success.

We were such a hit that we toured vaudeville shows all over the country and even in London. For our new acts, I started writing our music. Once we returned to the U.S., we entered into our second project, musical theatrical works. But it was different this time; Walker and I became the stars of Clorindy, or the Origin of the Cakewalk, in June 1898. This show had Will Marion Cook as a composer and Paule Laurence Dunbar as the lyricist and book writer. This would start our long-time collaboration with W.M. Cook and P.L. Dunbar.

The next time we collaborated was in 1903 for In Dahomey. What was extra special about this was the first all-black musical comedy on Broadway. The creative team this time was a little different. Of course, the talented Williams and Walker started with W.M. Cook Composing and P.L. Dunbar on the lyrics, but J.A. Shipp on the book. While Cook was the main composer this time, I also collaborated and included some of my compositional work. This was special for me because, for the first time, you could see the name Bert Williams on sheet music all over the country. Some popular songs include, On Emantionpation Day, Swing Along, and When The Moon Shines. Few of the numerous musical numbers. Actually When the Moon Shines was a popular song added to the show a year later for its revival in 1904. It is one of the first pieces that started to humanize us black people as it is two characters singing about love. Which is one of the things that people thought black people could not do. This musical is special to all of the cast (50 goddam actors on stage) and all of the creative team not only because we were all black, but the story was the push of the boundaries of what black people could be. Here I would also create my signature character, The Jonah Man. This was also the first story where our setting goes "back to Africa" that we would continue to use. I honestly think I need to visit because this grease paint is making white people think were friends.

Abyssinia. Now this was a whole different show. After the wild success of In Dahomey, we decided to push the envelope even more. The whole show was set in Africa — not like the vague "jungle" Africa that white folks liked to make up, but we really leaned into it. African animals on stage, completely African themes, lush set pieces, and our same creative crew: Will Marion Cook on music (of course), J.A. Shipp and Alex Rogers on the book and lyrics, and me throwing in my own music again.

This time the show and en entire original story and original score. Like, no borrowing, no adapting white works. All Black creative team, all Black cast, all Black-produced, and we’re performing for white audiences who barely knew Africa was a real place and not some made-up location.

In Abyssinia, George and I start off playing our usual minstrel characters, with all the dialect and comedy people expected from us — but here’s the kicker: the moment we "arrive" in Africa, all the African characters speak in perfect English. It flipped the whole stereotype on its head. White people were laughing that the "natives" were suddenly more articulate than they were. When we were trying to send a message.

That show had one of my biggest hits — Nobody. That song followed my signature “Jonah Man” persona: down on his luck, quietly defeated, but all heart. I always said: make ‘em laugh, make ‘em cry. “Nobody” did both. It was that character, that man who just wanted to be seen. It’s wild to think that character — the quiet, invisible guy — inspired Mr. Cellophane in Chicago years later. What I was doing wasn’t just entertainment, it was legacy.

Then came Bandana Land in 1908, which would be the final show George and I ever did together. We knew something was wrong. He was getting slower, forgetting lines, and slurring words. It broke my heart, man. But he powered through that whole tour. That show had a whole plot about a land scheme where we were conning white folks by selling them land, then threatening to build a Black amusement park next door unless they bought the rest at a higher price. I mean, come on, that’s brilliant. One of the standout moments was when I played a whole poker game on stage without saying a single word. All pantomime. Got a standing ovation. Ada (his wife) was there too, singing songs like Kinky and I'm Just Crazy 'Bout You. They lit up the stage together.

After that tour, George had a stroke. He developed a stutter, memory problems. We later found out it was untreated syphilis. He died in 1911. I still haven’t recovered.

I kept going. Headlined the Ziegfeld Follies — yeah, me, top billing, in an all-white production. That was 1918 at the Palace Theatre, the biggest vaudeville house in the country. Then the Schuberts poached me. I was everywhere. But in 1922, I collapsed mid-tour in Detroit. Died a month later.

So yeah, AITA for performing in “blackface” as a Black man to make fun of white people?