The curtain rises on Times Square where passersby tell us that New York is the center of the universe for would-be artists. Lenny, who is making his living as a waiter in a seedy diner, tells us that he is A Writer in New York. His Boss, on the other hand, is less enthusiastic about Lenny’s prospects. Lenore, working as a waitress in the diner while she tries to get a job as a dancer, is in love with Lenny for no good reason. She and Lenny describe the show he is writing, called Dragon Slayer. A knight named Florestan is frightened of dragons, but a magician gives Florestan a magic word that makes him invincible. Lenore asks Lenny to let her play Genevieve, Florestan’s love interest, but Lenny says she is not good enough. The customers in the diner reproach Lenny for being cold. He explains that he was tasked by his Granddad with being a Broadway star and is only fulfilling his destiny. Lenore, alone, sings I Love A Jerk. Genevieve visits and tells her she needs to consider other men. She parades out imaginary candidates, who suggest Dance With Me. Lenore rejects them all. She likes Genevieve better. Genevieve is not prepared to be Lenore’s lover, but she will be her friend

Lenny has written a Love Song to be sung by Genevieve. Genevieve appears in Lenny’s imagination singing the song and Lenny falls in love with her. She reproaches him for falling in love with an imaginary woman and says that Lenny doesn’t know anything at all about real love. In Somebody Likes You, she tells Lenny not to ignore Lenore. Lenny is impressed and asks Lenore out for pizza. At the pizza place, a sinister figure appears from the shadows and pulls Lenny away to talk about an offer. He is the Boss disguised as Sparafucile, the villain from Rigoletto. Sparafucile can get Lenny’s show before his brother-in-law the famous producer Max Bialystock for a price. The price is his life savings…and that of Lenore. Lenny returns to the table and asks Lenore for the money. Lenore turns Lenny down; she has no money. Lenny insults her, and she sings of how Shabbily he has treated her. She is through with him. Lenny declares that he doesn’t need Lenore, because It’s Enough to be a famous writer. The next day, Lenore is cold to Lenny, who is still preoccupied with his show. The Boss nags him about his absent work ethic. Lenny complains that he wants more Appreciation and the Boss fires him as the act ends.

Act Two opens with the Boss explaining that in Every Story Written, the villain is the most important character, because it is the villain who moves the plot. Sure enough, when Lenny has his appointment with Max Bialystock, the producer is played by the all-purpose villain, the Boss. Bialystock tells Lenny, Your Work Is Junk. Lenny is crushed. Lenny and Lenore, in different places, sing how Alone they are. Lenny encounters Genevieve, who tells him in Magic Word that he bet everything on the magical attraction of fame while throwing away the real magic, Lenore’s love. Lenny muses that he has no job, no dream, no girlfriend. Genevieve helps him with a plan to win Lenore back; Lenny will write a Ballet for her, because she is a dancer. Lenny meets Lenore and apologizes for having treated her Shabbily (Reprise). He gives her the ballet, and Lenore runs off crying, which perplexes Lenny. Now unemployed and hopeless, he joins other street people and they reprise Writer in New York. Lenore comes back with news. She has gotten a part using Lenny’s ballet, and the producer wants to talk to Lenny about a job. Lenore is willing to give Lenny another chance. They reprise It’s Enough, but this time it’s enough to find love in this crazy world. Lenore, Lenny, and the company reprise Love Song.