The six Queens introduce themselves performing at a pop concert, telling the audience that the position of lead singer will be the prize for whoever they determine had the worst experience at the hands of their common husband, Henry VIII. Catherine of Aragon recounts how Henry wished to annul their marriage and place her in a nunnery when he began lusting after Anne Boleyn, much to her humiliation. In turn, Anne mocks Catherine of how Henry wanted her instead but then complains of the infidelity Henry partook in, which lead to Anne committing her own affairs and ended up beheaded in return. Jane Seymour announces it is her turn partake in the contest, but is mocked for having had an easy time with Henry. However, while admitting she may have been the only one Henry truly loved, Jane claimed the love was conditional on her having produced a male heir and that she had stood by him despite knowing his many faults.

Themes relating to ideas of female beauty are explored in Hans Holbein's painting studio, where the Queens parody a dating app site by presenting a choice of three women for Henry. He chooses Anna of Cleves but soon rejects her and annuls the marriage. She makes a show of complaining about living in a beautiful palace in Richmond with an enormous fortune and no man to tell her what to do but in reality ends up bragging about it. The Queens question this, and Anna decides to drop out of the competition in favor of returning to her lavish lifestyle. The Queens then belittle Katherine Howard for being "the least relevant Catherine", but she in retaliation mentions flaws in the other Queens' reasons for winning before recounting her romantic history, having had many suitors even as a child, and at first relished in her attractiveness but reveals the emotional trauma and abuse she faced in each of these relationships.

As the Queens continue to fight over who is the true winner, Catherine Parr questions the point of the competition which defines them by their connection to Henry rather than as individuals. The Queens, however, do not listen and continue to argue. Frustrated, Parr tells of her separation from her lover and arranged marriage with Henry but mainly acknowledges her accomplishments independent of Henry. The other Queens, realizing they have been robbed of their individuality, abandon the contest and declare that they do not need his love to feel validated as people. They use their remaining moments on stage to rewrite their stories, singing together as a group rather than as solo artists and writing their own “happily ever afters.”