Act I
In 1922, Nick Carraway, a Midwestern young World War I veteran, arrives in New York to work as a bond salesman. He is lucky to find a cheap rental in a cottage adjoining, and owned by, his mysterious neighbor, Jay Gatsby. Nick is awestruck at the wealth and excess on display, particularly Gatsby's palatial estate ("Roaring On"). Nick travels directly across the bay to the home of his cousin Daisy and her husband, his old-money Yale college acquaintance Tom Buchanan, a former football star. Daisy introduces Nick to her friend, golfer Jordan Baker, a vivacious and independent young woman. Daisy is pleased to see Nick flourish in New York and implies that her marriage is unhappy ("Absolute Rose"). Daisy and Jordan learn that Nick has received an invitation to one of Gatsby's famous over-the-top parties; Daisy becomes pensive at the mention of Gatsby's name, but Jordan is eager to experience the lavish party and asks Nick to take her ("New Money"). During the party, Gatsby sends for Nick; they meet privately in the study, where Gatsby shows Nick his war medals for valor. Gatsby confesses that he has built his fortune and estate solely to win back his pre-war sweetheart, Daisy, whose father had rejected him as a suitor for Daisy before the war because of his poor social position. He asks for Nick's help in reacquainting them ("For Her"); Nick is hesitant, finding the overture distasteful, since his cousin is married.

George Wilson, at his run-down garage and gas station in the shadow of a gigantic billboard, questions his position in life ("Valley of Ashes"). George receives regular shipments from Gatsby's shady business associate, Meyer Wolfsheim. Tom visits the garage to get gas, and all realize, except George, that his wife Myrtle is Tom's mistress; Myrtle hates being poor and is excited to be the mistress of a rich man ("Second-Hand Suit"). Meanwhile, Daisy and Jordan discuss Tom's indiscretions and the state of her marriage; Jordan is staunchly against getting married ("For Better or Worse").

Tom takes Myrtle and Nick (who thought they were going for a day at the Met) to the Manhattan apartment of Myrtle's sister Catherine, and they carry on their affair. Tom breaks Myrtle's nose during an argument; Nick despises Tom's brutality and snobbery and decides to reintroduce Daisy and Gatsby ("The Met"). As Gatsby had suggested, Nick invites Daisy to an afternoon tea. Gatsby is to casually drop by, but he panics and provides Nick's cottage with lavish decorations and expensive food ("Only Tea"). Daisy is pleased to see Gatsby, and the two converse privately inside the cottage while Nick and Jordan flirt outside during a rainshower and share a kiss. Daisy goes with Gatsby back to his mansion, finds out that her father had destroyed Gatsby's wartime letters to her, and the two begin an affair ("My Green Light").

Act II
Wolfsheim reflects about illicit acts and secrecy ("Shady"). Nick and Jordan's relationship deepens; Jordan proposes to Nick. ("Better Hold Tight"). Gatsby, convinced that Daisy will leave Tom for him, begins to plan a party recreating their relationship during the war, neglecting his business affairs with Wolfsheim ("Past Is Catching Up to Me"). At the party, Gatsby hires performer Gilda Gray and dances with Daisy as Tom watches enviously and converses with Wolfsheim ("La Dee Dah with You"). Daisy tells Gatsby that she wants to run away with him ("Go"). Tom demands that Daisy leave but is persuaded to visit the Plaza Hotel with Nick, Jordan, and Gatsby instead. Tom, driving Nick and Jordan, stops at the Wilsons' garage; Jordan loudly says they are going to the Plaza and Myrtle (who, unbeknownst to them, is pregnant) hears.

At the Plaza, Daisy and Gatsby's affair comes to light, infuriating Tom. Gatsby demands that Daisy swear she never loved Tom, but Daisy cannot; she becomes more reluctant to leave Tom after Tom reveals that Gatsby's fortune is from bootlegging alcohol ("Made to Last"). Everyone leaves the hotel. Myrtle has been walking to the Plaza, thinking about her pregnancy with Tom's child. She is hit and killed by a yellow Rolls-Royce ("One-Way Road"). Tom sees Myrtle's body being carried away by the police. Jordan and Nick realize that Gatsby's car killed Myrtle, but Jordan wants to stay quiet. The ethical Nick is disappointed and calls off their wedding. Tom tells George that Gatsby owned the car; George despairs ("God Sees Everything").

Daisy retreats into her own home. Nick finds Gatsby alone at his mansion. Gatsby tells Nick that Daisy had been driving the car. He thinks Daisy will return to him and says he intends to take the fall. Nick leaves as Gatsby begins to take a swim. George arrives and shoots Gatsby and then himself ("For Her" (reprise)). Nick is the only friend at Gatsby's funeral as people gossip about his death ("New Money" (reprise)). Nick confronts Daisy, who is now leaving with Tom for Honolulu, about her abandonment of Gatsby. Daisy tells Nick that she hopes her young daughter has no further ambitions beyond becoming a beautiful and docile rich wife ("Beautiful Little Fool"). Deciding to return to the Midwest, Nick visits Gatsby's abandoned mansion one last time and thinks he sees the man briefly standing on the dock ("Finale: Roaring On").