Gypsy is based on the memoirs of Gypsy Rose Lee, a self-invented personality who worked her way up from burlesque to Broadway with a self-mocking intelligence that today we'd call post-modern. She wrote books, appeared in films and radio and TV shows, and eventually became famous for being famous. (She was, for example, the subject of a whole song in the Rodgers & Hart musical Pal Joey.) She solidified her legend by committing it to print, in the form of her memoir Gypsy, which tells the who-knows-how-true story of her childhood, growing up in the shadow of her very talented younger sister June and being pushed into show business by her indomitable stage mother, Rose.
It is Rose who is the leading character of the musical Gypsy, which traces a journey that begins in Seattle, Washington in the waning years of vaudeville. We watch Rose maneuver and scrape to get her daughters into the "Big Time," and eventually she does, landing them, with the help of her agent/boyfriend Herbie, in the Orpheum Circuit and eventually in a grand theater called Grantzinger's Palace in New York City. But Grantzinger tells Rose that the he doesn't want the whole act, a fanciful if tacky affair worked up by Rose called "Dainty June and Her Farmboys"; all he wants is June, who he thinks can be trained and molded into a real actress. In the play's pivotal moment, Rose refuses in a rage of invective: June belongs to her, not to Grantzinger (not to herself either); she storms out of Grantzinger's office and effectively destroys the one real chance that June has to achieve the dream of stardom that Rose has supposedly been nourishing all these years. It's a complicated and defining moment in Gypsy, one that makes it clear that what feels at first like a colorful and light-hearted chronicle is really a rich and difficult tale about parents and children and dashed hopes and dreams and oh so much more.
What happens next--and if you don't know the show and don't want me to give it away, please skip this paragraph--is that June runs away from home and Rose turns her considerable energies to the older daughter, Louise, determined now to make her into a star. But vaudeville is pretty much dead by now, so the only booking that Herbie can get the new act (called "Rose Louise and Her Toreadorables") is in a second-rate burlesque house in Wichita. (They're the act that's supposed to "keep the cops out.") Rose, Louise, and Herbie are at first mortified at where they've landed, but they decide to tough it out; after the booking, Rose promises, she will marry Herbie and leave her dream behind her. Then the star stripper goes missing one night, and Rose jumps into the breech. "My daughter can strip," she says, and in a matter of minutes, Gypsy Rose Lee is born. The rest, literally, is history. The show ends with Rose coming to terms with some of what's happened to her (in the mammoth "Rose's Turn," which has been described as a musicalized nervous breakdown); and then, perhaps, coming to terms with her now-grown and independent daughter.
Rose is like the Everest of musical heroines: she's got an enormous personality and she sings a lot—seven big numbers, all written for the distinctive clarion voice of Ethel Merman, who originated the role on Broadway in 1959.