The show opens on a medicine show in 1890, where a charismatic Young Bert Williams is serving as barker and successfully convincing the crowds to buy a snake oil cure-all (“Johnson’s Mystical Oil”). After his song, he discovers his father was watching, but before he can explain why he’s missing school, his father embraces him, recognizing his son’s incredible gifts. While he fears for how a racist society will treat his young son, Young Bert reassures him that he’ll use humor to soften their hearts (“I Can Make ‘Em Laugh“).

In 1895, Charlie, a charismatic, white song and dance man, sings a vaudeville song in rehearsal for Florenz Ziegfeld’s latest vaudeville show (“How Can I Choose”). Meanwhile, Bert is waiting to audition for a San Francisco vaudeville show, when he meets George “Nash” Walker.

Later that year, Bert and George are performing in a vaudeville show and exit the stage to boos. George is too harrowed to go back on for their next number. Bert, forced to go on alone, searches for a prop or gimmick he can use for his suddenly solo act. He sees the burnt cork and petroleum oil mix that the white comics are using to “black up” (put on blackface) and, despite George’s protestations, he blacks up, goes onstage, and performs a hit number playing the white-invented caricature of Blackness, the “coon.” (“The Coon Can”)

Later that year, George comes over to Bert’s apartment with the news that he fired their manager who doesn’t support their dream of performing in the New York vaudeville scene. Bert is irate until George reveals that he already found new representation and they have tickets in hand for New York. (“Say Goodbye”) They arrive at a large Vaudeville theatre and are stunned into silence, but they summon their courage and commit to risking it all for the chance to make it big. (“We’re Gonna Fly”)

By 1896, Bert and George are performing regularly as “Two Real Coons,” with George playing the savvy straight man and Bert playing the comic dunce character, Jim Crow. Meanwhile, Charlie is hard at work rehearsing for a Ziegfeld production after everyone else has gone home. He reflects on his journey to Ziegfeld, a surrogate father of sorts to him, and he sings about how he left the family who disowned him for going into show business, all for the allure of the Broadway Stage. (“Couldn’t He See”)

In 1896, Bert and George meet Aida and Lottie while doing a photo shoot together for the American Tobacco company. The foursome hit it off and in the next year, they introduce New York audiences to their version of the Cakewalk, choreographed by Aida, and it becomes an international sensation, leading to a worldwide tour. (“Cakewalk”)

Aida and George marry, as do Bert and Lottie, but George is prone to cheating on Aida. While grabbing a cigarette outside of the theatre showing their soon-to-be hit Sons of Ham, a white mob enters and attacks George during a race riot. In the hospital the next day, Bert and Aida keeps George company while he recovers from serious injuries. Bert tries unsuccessfully to encourage George to join him in taking solace in books, sharing his well-worn copy of John Ogily’s history of the African continent and people. Bert claims that the book proves that “Every Pullman Porter” is descended from a king.

Bert and George go on to a dizzying string of successes, starting in 1903 with In Dahomey, through which they finally reach their dream of performing on Broadway. George sings his hit tune “Cocoa Clyde” in this show. The team heads to England for a command performance for the royal family, where Bert and George replay Bert’s early days in the medicine shows, now as a sketch for “Hansen’s Magical Oil,” which can lighten the skin, thereby improving the fortunes of people of color. Bert sings his hit song, “Jonah Man,” playing the role of the unluckiest man around. At another show, George is again performing “Cocoa Clyde” (Reprise), when he starts to confuse the words. His speech degrades to an alarming point until he stops singing entirely. Bert has to march the stupefied George offstage. George has suffered a syphilitic stroke.

Bert and Aida both strike out as solo acts, while Lottie stays at home. Bert visits George, who’s being treated for syphilis. Bert shares that he got asked to join the Ziegfeld Follies, but at a cost, since Black audiences still can’t attend the shows. Bert and George worry that Black audiences will feel betrayed.

Charlie is rehearsing for the 1910 Ziegfeld Follies show, singing a song about how you don’t have to worry about the world’s troubles, when you can just dance and be happy. (“When You’re Dancing”) After their rehearsal, Ziegfeld brings Bert in and introduces him as their new headliner to the stunned ensemble – a Black man has never performed in a Follies show before, let alone as a headliner.

Bert and Follies comic Leon Errol have hit it off and are brainstorming ideas for a comedy routine. Bert gets called into Ziegfeld’s office to learn that several members of the Follies cast have revolted against a Black man performing in the Follies, with Charlie at the fore. They threaten to leave the show if Bert isn’t fired. Ziegfeld calls their bluff, saying that Bert’s the only performer in the show who’s irreplaceable. Bert is made to witness the exchange and when the white cast members file out, stunned, Bert and Ziegfeld alone. Ziegfeld exits after the others, saying to Bert, “You better be worth it, boy.” Charlie is leaving the theatre, stunned at this turn of events convinced Ziegfeld is making a mistake that will tarnish the good name of the Follies. Bert is shaken, but ultimately recommits to using humor to advance the cause of racial uplift. (“I Keep Them Laughing”).

The act opens with the 1911 Follies, with a singer extolling the beautiful girls that were Ziegfeld’s trademark. (“The Wonder of Beautiful Girls”) Bert and Leon perform the sketch they had been brainstorming. Bert plays a drunk Electrobat Taxi driver to Leon’s British tourist.

Charlie is distraught about the separation from Ziegfeld, to whom he had long been loyal. His manager convinces him to accept an offer from the Schuberts, Ziegfeld’s chief competitor, in their new offering, The Passing Show.

Ziegfeld hires a young comedian, Eddie Cantor, who hero worships Bert. Meanwhile, Aida is choreographing a show of her own and she comes down hard on a female dancer who’s dancing the Cakewalk as a comedic caricature, like Bert had. Aida insists that the dance be done with dignity in her show. Aida is called away from rehearsal by a phone call to learn that George has died. Bert gives a eulogy for George, identifying him as a man of uncompromising vision and business sense, where he felt he had too little of either. (“We’re Gonna Fly – Reprise”)

It’s 1917, and the writers are arguing about sketches for Bert, trotting out the same old stereotypes of people of color. Bert is hardly given a voice in the room. In the 1917 Follies show, Bert performs a patriotic number during wartime about all of the Black soldiers who were quick to enlist. (“You’ll Find Ol’ Dixieland in France”) 

It’s 1919, and Bert takes a meeting with his manager, saying he wants to perform serious dramatic roles instead of the minstrel-based comedy for which he’s become famous. His manager reluctantly agrees on the condition he first go on a multi-year national tour to help finance what he anticipates will be a career-ending move. While Bert gets ready to leave, Lottie tries and fails to persuade Bert not to do the tour and to instead stay and enjoy the life they’ve built together.

Eddie and Bert head out on the tour, but as the troops return home, the soldiers of color are greeted with race riots and racism; nothing has changed. Between this and Bert’s own poor treatment despite his fame, Bert is left feeling hopeless and already exhausted, even though the tour is just getting started.

In 1921, Bert and Charlie are both giving interviews. While Bert is asked pointed questions about race in America, Charlie’s largely focuses on his upcoming marriage and his success with the Schubert shows.

In 1922, well into his tour, Bert is backstage trying to sleep off a bad cold that’s hung on for four weeks before that evening’s performance. A reporter, Ida B. Wells-Barnett, knocks and says she wants to sell him rags for his ragman costume. Bert directs her to the costumer, but she insists he’ll want to see them himself. She reveals that all of the rags were torn from the bodies of Black men who were lynched. She’s been traveling the country chronicling their stories. She blames Bert for perpetuating racial stereotypes and supporting a dehumanized vision of people of color. (“You Want Rags”) 

Later that evening, Bert is in bad shape. He’s feeling much sicker, both physically and spiritually, after his confrontation with Ida. His lawyer is there and tells him not to go on, but the theatre owner insists and Bert agrees. He’s left alone to black up and prepare to go on, but is now questioning his choices and his own culpability for potentially contributing to racism in America. (“This is How It’s Done”)

Bert manages to get through the show, but is so ill by the end of it, he collapses backstage, while the audience chants for an encore. Despite Eddie’s protestations for his friend, the theatre owner says that Bert always performs an encore and he needs to tonight. Bert agrees and stumbles onto the stage. While performing his trademark number, “Jonah Man” (Reprise), he staggers and sweats profusely, removing much of the blackface as he blots his face with a handkerchief. The audience thinks this is part of the bit and, even as Bert collapses to his knees, they laugh hysterically.

Lottie is by Bert’s side in a hospital room. Lottie tries to get Bert to hold on, but he’s too far gone. He dies with her at his side, as an offstage chorus sings. (“I Keep Them Laughing – Reprise”). Projected images of the next 100 years of Black struggles and triumph fill the stage around Bert.