After a rousing overture, the curtain opens on a picket line and demonstration in New York City’s Garment District in 1937. Fashion Avenue’s delivery boys and shipping clerks forcefully demand $15 per week, but the police arrive, disbanding the protestors.
In the office of dress manufacturer Maurice Pulvermacher, harried secretary Miss Marmelstein juggles disgruntled clients, upset about the strike. Mr. Pulvermacher is overwhelmed (“I’m Not A Well Man”). Harry Bogen, a brash young shipping clerk, barges into the office and proposes a solution: Pulvermacher can ignore the strikers and instead hire Harry’s new company, The Needle Trades Delivery Service. Pulvermacher begrudgingly signs the contract.
In the street, Harry’s friend Tootsie reminds him that the Needle Trades Delivery Service doesn’t even exist yet. Tootsie contributes $500 to start up the company, and Harry says he knows where to get more funds. Bluntly, Harry shares his cynical philosophy: the only thing that counts in this world is money (“The Way Things Are”).
Harry returns to the Bronx to meet up with his old friend, Ruthie Rivkin. Ruthie is clearly still smitten with him (“When Gemini Meets Capricorn”) and she agrees to invest in his company. In his mother’s homey kitchen, Harry shares the good news and presents his mother with a new hat. Mrs. Bogen is shocked and delighted by the gift and her son’s sudden success. As time passes, Harry continues advancing professionally, and his gifts grow more and more lavish (“Momma, Momma, Momma”). Finally, Harry asks his mother to cook up a lavish dinner; he plans to start a dress business, and he wants to impress his potential partners with a home-cooked meal.
At the Club Rio Rhumba, Harry interrupts his date with actress Martha Mills to conspicuously sell his half of the Needle Trades business to his partner, Tootsie. When Tootsie leaves, Harry admits he’s made a killing; the business will soon be worthless. Martha, admiring Harry’s ruthless ambition, recognizes an opportunity (“The Sound of Money”).
At Harry’s home-style dinner, Mrs. Bogen’s cooking charms all the guests: gifted salesman Teddy Asch, top dress designer Meyer Bushkin and his wife Blanche, Harry, and the unassuming, faithful Ruth, whom Harry has invited support his image as a stable family man. Using Yiddish terms of endearment, Mrs. Bogen introduces everyone, and they celebrate with a traditional kazatske, or dance (“The Family Way”). Teddy and Meyer commit to the new partnership, dubbed Apex Modes, Inc., and the guests say good night. Ruthie stays to help Mrs. Bogen clean up, and she says she’s certain that Harry will propose to her now. Mrs. Bogen, wise to her son’s charm and ambition, warns Ruthie not to count on him (“Too Soon”).
After spending a pleasant evening with Harry, Ruthie hints at marriage (“Who Knows?”) and offers to invest ten thousand dollars in Harry’s new business. Harry refuses her offer and tells her, “What you’re entitled to get for your ten, I can’t give.”
Weeks later, the Apex Modes office is abuzz. Miss Marmelstein – who has left Pulvermacher to work for Harry – assists the staff as they prepare for the company’s first show for wholesale buyers. Harry oversees the models and instructs Miss Marmelstein to cut check for client gift and other expenses, including a diamond bracelet. Mrs. Bogen and Ruthie arrive, and Harry gives them a tour. Teddy Asch is appalled and angered by Harry’s extravagance, but Harry assures Teddy and Meyer that soon they’ll all be rich.
Meyer, who has been designing and building dresses for weeks, feels exhausted and overwhelmed, but his loyal wife Blanche reinvigorates him with a simple affirmation of her love (“Have I Told You Lately?”). Blanche and Ruthie join the staff as they all prepare for the big show (“The Ballad of the Garment Trade”). Teddy serves as emcee while the models – including Harry’s showgirl, Martha – walk the runway in an elegant fashion show. After the show, everyone waits behind the scenes, nervously awaiting the results. Teddy enters with a fistful of orders – they are a hit! As everyone celebrates, Harry gives Martha a diamond bracelet, and she gives him her apartment key. “Two years ago, you were just another poor slob from the Bronx,” Harry tells himself. “And tonight, you’re gonna sleep with an actress!”
In his luxurious new penthouse apartment, Harry hosts the bar mitzvah of Blanche and Meyer Bushkin’s son, Sheldon. Harry presents the boy with a gift: a check for one year of college tuition (“A Gift Today”). As the others celebrate, Teddy pulls Harry and Meyer aside: Harry’s check was drawn on the company account. Harry tears up the check, blaming Miss Marmelstein for a clerical error. When Harry steps away, Meyer insists that they all trust each other. “You do the trusting,” say Teddy. “I’ll do the looking.”
At the office, business is brisk, and all the pressure seems to rest on the shoulders of beleaguered “Miss Marmelstein.” Teddy enters, enraged. With cancelled checks in hand, he angrily confronts Harry about his unethical spending from the company account. When amiable Meyer refuses to condemn Harry, Teddy quits the firm. Seeking a way to siphon off funds, Harry convinces the gullible Meyer to open a second bank account in his name. Meyer, naïvely trusting his friend, concedes.
Things begin to close in. Miss Marmelstein warns Meyer that their accounts are in bad shape. Ruthie warns Harry that his creditors have hired the lawyer she now works for. She also tells him her boss has proposed to her (“A Funny Thing Happened”), but Harry is unmoved. At the Club Rio Rhumba, Martha tells Teddy that her recent checks from Harry have bounced. Teddy, however, has made a bundle by selling his share of the company, so Martha resets her sites on a new man (“What’s In It For Me?”).
Things are beginning to fall apart at Apex Modes, and Miss Marmelstein desperately tries to maintain order. Teddy arrives and offers to buy out the stock at 15% of its value. Miss Marmelstein refuses, but she can’t forestall the inevitable: bankruptcy (“What Are They Doing To Us Now?”).
At his mother’s house, Harry claims innocence as his partner Meyer faces jail time. Taking responsibility for her own part in this mess, and ignoring Harry’s excuses, Mrs. Bogen slyly manipulates Harry into doing the right thing (“Eat A Little Something”).
Miss Marmelstein has returned to her former position at Pulvermacher’s office, and she tends to him as he laments his sorry health. Harry enters, seeking money to bail out Meyer. Pulvermacher agrees to lend Harry the money, provided Harry takes over his company. Soon after, on the street, Ruthie and Harry reconcile. Harry says he knows a place where they can get a great meal—his mother’s house. Tentatively, they set off together as the curtain descends.