(Note: Song titles in white are clickable links to the demo of that song, or use the SoundCloud playlist.)
A young man, Basset, arrives at the house of Jack and Hester Dolloway, to find that You Can’t Have Too Much Christmas. Jack and his children, Joan and Paul, welcome Mr. Basset into their home. Hester is secretly tormented by the frivolity (I Can’t Breathe, You Can't Have Too Much Christmas part 2). Later that night, ten-year-old Paul wonders what his large, mysterious present could be ("There's Something in the Paper"). Christmas morning, the family all open their many, many gifts (Please and Thank You Please), culminating in Paul opening a creepy antique wooden rocking horse.
Weeks later, fourteen year old Joan is playing at her new piano, and Jack is leaving on another of his business trips. He tells her that even when he’s gone, "Jack & Joan", are what’s most important to him. Two Repo Men come to the house and begin to take various possessions, including some of the extravagant Christmas presents. Hester’s brother Oscar— checkbook in hand— is able to stop them from taking everything, particularly saving Joan’s piano and Paul’s rocking horse. After Oscar and the Repo Men leave, Paul sees how upset Hester is, and gives her his most valuable possession, his bag of "Marbles".
A week later, Paul has mysteriously fallen ill, and had a fever dream last night where he heard the name, Persephone, but doesn’t know what it means. To cheer the sick ten-year-old up, Basset tells the exciting story of The Racing Horse Winner. Paul realizes that Persephone is the name of the slow horse in Basset's story, and convinces Basset to bet a single dollar (of Paul’s) on Persephone the next time Basset is at the track.
In February, Hester explains to Paul that some people are "lucky", and attract money, and some people are not. She leaves Paul alone in his room. Downstairs, everyone is fighting. Hester is angry with Jack for not holding down a job. Oscar is angry with Hester for constantly asking him for money. Jack is angry with Hester for her excessive spending. Joan wants someone, anyone, to pay attention to her piano playing. Basset is trying to get Paul to open his door to give him the name of the horse to bet on. Inside his room, Paul is riding his rocking horse, begging it to "Take Me to Where There Is Luck". Paul is transported, riding furiously as if in a dream. He sees the name of the winning horse. He collapses, exhausted.
Paul is sick, lying on the couch. Basset tells Oscar about the bets he’s been placing for Paul. Oscar promises to try to put an end to it. Paul, very sick (and very persuasive), tells Oscar that his original dollar bet has grown to eleven hundred dollars, and Paul wants to get that money to Hester. Oscar and Paul concoct a plan to say that a long lost (imaginary) relative has passed away and left Hester the money. In the kitchen, Jack tries to make peace with Hester by offering her a cup of coffee, reminding them of their first passionate moment together while spending "A Day at the Fair". Oscar interrupts to tell Hester that the family’s financial problems are solved, due to the passing of a long-lost (fictional) relative. Hester insists that they hold a memorial service the next day. At the memorial, Hester is deeply saddened, even as Oscar, egged on by Paul, spins a more and more ridiculous yarn about their dear departed Aunt Lottie. Paul gives Hester the money the family so desperately needs. Hester announces that she will use the money… to remodel the house!
The remodel has stalled; the money has run out. Basset, and the Dolloways’ housekeeper, Miss Wilmot, have not been paid. But they have been assured that everything will be fixed in about "Two Weeks". Jack is about to leave the house, when Joan and Paul ask him why he and Hester fight so much. He explains his “live for today” outlook on life (Tinkertoys) to his children on his way out. Paul thinks that this means his father wants to leave the family, so Paul rides his horse, but is not able to see the name of the winner. In spite of that, he asks Basset to bet all the remaining money on today’s horse race. Basset advises against it, but agrees.
Later, Hester wanders around the house in her bathrobe, thinking back to the rocking horse "Music Box" her parents gave her before they died. The Repo Men come back to the house. They listen to Hester, comforting her. Their compassion turns to passion, and the three begin a romantic liaison. Paul and Joan walk in on them. Hester is mortified and runs into the kitchen. Oscar and Basset come in. Basset stays with the children, and Oscar joins Hester. Basset tells Paul that the horse Paul bet on lost the race, but Basset only bet half the money. Paul, upset, goes up to his room. Hester joins him, telling him that whatever happens to their family, it is not his fault, or responsibility. Paul wants to be alone. Hester, feeling rejected, leaves. Paul rocks feverishly.
A week later, Paul has again taken ill, and is in bed. But he won his most recent bet, so he thinks his illness is worth it. Downstairs, Miss Wilmot is fed up with not getting paid, and quits. The Repo Men show up while the family is in the living room. Only Jack is unaware that these men have been taking the family’s possessions, and that these men had an interrupted romantic encounter with Hester. The Repo Men tell Oscar that the house is about to be foreclosed upon. Jack demands to know what is going on. Joan steps up, and dramatically threatens to reveal all to Jack ("For Once, It’s Joan"). But she doesn’t tell Jack that Hester has been unfaithful. The family is in crisis, both financially and emotionally. Paul tells everyone that he will make it all better this Saturday: The Kentucky Derby. Hester says that she believes in him. In fact, she’s going to throw an extravagant Derby party to celebrate.
Hester, Paul and Joan are dressed up for the Derby party. Hester doesn’t know how Paul has been getting the money, but she realizes that he has been her 'angel', and will again save them from financial ruin. When Hester steps out, Jack tells the children that he understands that Hester is unhappy in her life, and about being a mother and a wife. And Jack is going to take the children to live in England, where he has been having a secret relationship with a kind woman. Hester overhears this, and says she won’t let Jack take the children, and that she knows about his infidelity. Joan tells Jack about Hester’s tryst with the Repo Men. Jack takes the children. But Paul insists that he will stay with his mother. Joan and Paul share tearful goodbyes, and promise to see each other next Christmas. Jack and Joan leave. Hester is moved that Paul chose to stay with her. Hester insists that they are still going to have their Derby party, and goes to finish getting ready. Paul and Oscar go over their plan: Oscar will be waiting by the phone to have Basset, at the track, ready to place the winning bet. Paul goes up to his room and rides the horse, more furiously than ever. It is draining the life out of him, but he will not relent. Hester wanders up to Paul’s room. She walks in, finally learning what Paul has been up to, where the money has been coming from, and why Paul has been so ill. Paul cries out the winning horse’s name. Oscar tells Basset, who places the bet. Paul collapses into Hester’s arms. She commands Oscar to run to get the doctor. Hester finally is able to see how much her son loves her. He goes limp in her arms ("A Dream for Paul"). For the first time, Hester tells Paul she loves him. Could those three words save his life?