Gypsy was based on the memoir written by Gypsy Rose Lee and matches much of her real life. The musical thrust many of its songs into popularity, including "Small World," "Everything's Coming up Roses," and "Let Me Entertain You." Throughout its various Broadway revivals, Gypsy has won six Tony Awards and eight Drama Desk Awards. Several well known film and television actors have played the lead role of Rose, including Angela Lansbury, Tyne Daly, and Bernadette Peters.
Gypsy tells the story of Rose, a stage mother who is determined to make stars out of her two children, June and Louise. During the Great Depression, Rose has developed an act for the two girls. The act has one song, "Let Me Entertain You," that is sung repeatedly. Despite her determination, Rose cannot find the success she seeks until she and the girls move to Los Angeles and Rose meets Herbie, a manager. After seducing him with ideas of a relationship and future marriage, Herbie agrees to manage the act.
The act does end up becoming successful thanks to Herbie, but the quartet lives in the wrong end of the vaudeville era, and the genre falls out of popularity as the years go on. Herbie is able to come to the rescue with a contract from Mr. Grantzinger for a show in New York City, but Rose does not appreciate the terms of the contract, and the group continues touring. Eventually, June runs off with a boy from their act, and Herbie tries to convince Rose to marry him and end the act. Instead, she declares that she would make Louise, who she had nearly always ignored up until this point, a star.
In the second act of Gypsy, life is miserable for Louise as Rose tries to make her be June. After several years, Herbie is able to get a short-term contract, but the trio realizes when they arrive that the venue is a burlesque house. Rose finally agrees to marry Herbie and leave show business to give Louise a normal life, but she cannot resist when the house manager is looking for a replacement after his star is arrested for solicitation, and she suggests her daughter. Herbie, disgusted by Rose's actions, leaves her. Louise finds success with the audience by taking the advice of other strippers in the house, and uses a "gimmick." For Louise, it is a strip-tease. In one of the final sequences, Louise has become a burlesque star, but her mother is shoved to the sidelines more and more. Rose fantasizes about being in the limelight herself, but finally realizes the long-standing self-centeredness that has led to her and Louise's current situation.