Surrounding Ragged Dick in the illustration above are Ben the Luggage Boy, Rufus the Newsboy and Mark the Match Boy.
A show curtain or olio, painted in the style of productions of the Old Bowery, featuring an unfinished Brooklyn Bridge and the skyline of New York City in 1876. Prominently displayed: "1876. WALL STREET IS KING AND VIRTUE ITS OWN REWARD."
It's an early spring morning in Lower Manhattan. The street dramatically comes to life, as the cast interacts while while complaining about the state of their fair city. (The Good Old Days) Afterwards, Richard Hunter "Ragged Dick" a bootblack, is discovered sleeping in a wooden crate. A policeman wakes him. It's a friendly routine.
As Dick dons his unusual wardrobe ("This coat was once worn by George Washington, he wore it crossin' the Delaware!"), Mickey Maguire, a shiftless kid from the neighborhood, comes asking for a loan. Together they meet an awkward first-time bootblack, Henry Foswell, to whom they each give some pointers. As Dick sets off to get customers for all three, he presents his sales pitch (Shine). The number makes it clear he is no ordinary street kid; along with an odd nickname, he has charisma, a unique shoeshine box, and a gift for getting business. Above all, unlike Mickey, he doesn't lie and he doesn't steal. During the number, Dick gets customers for all three as "Good Old Days" and "Shine" become one shoe-shining number.
After being insulted by a potential customer, Dick encounters Allen Carlisle, a well dressed gent who has witnessed the insult. Unexpectedly, he offers Dick a few pointers on bootblacking and asks for a shine. As he polishes the boots, Dick is lost in admiration for this interesting fellow and vows that he too will one day climb higher (Respectable). Carlisle pays him a dime ("What a beautiful thing!"), twice his usual fee.
Noticing an expensive suit in the window of Silas Snobden, Inc. "a haberdashery" Dick asks about buying it one piece at a time, starting with the colorful pocket handkerchief. Snobden happens to be in desperate need of an office boy, and he's so impressed by Dick's honesty, attitude and intimate knowledge of the streets that he persuades him to retire from the shoe business to work in his shop. Snobden's chief clerk Gideon Chapin and his assistant Higgins are appalled, but reluctantly instruct Dick in his new duties (Silas Snobden, Inc.) Dick is awarded the Silas Snobden jacket, loaded with packages sent out the door.
On the street soon after, he runs into Luke Gerrish, newly released from prison. Gerrish had been married to Dick's now-deceased mother. Prison has not changed him, and he mocks Dick for believing that hard work will give him a future (Cock and Bull) but Dick isn't buying and he leaves to continue his deliveries. But Gerrish sees an opportunity in his chance meeting with his stepson.
On a nearby street where she shares a shabby room with Gerrish, Stacia Jane Hauser, a young seamstress, buys a cheap Chinese lantern from a street stall. As she carefully carries her prize home, she wonders when she will finally hear Gerrish declare his love for her (Maybe Today).
Meanwhile Henry Foswell has been failing as a bootblack and Dick, to celebrate his new job, treats him to a meal in a saloon. It's filled with Wall Street bucks and despite Dick's youth and appearance he convinces them he and Foswell are a couple of active investors. The young business men shower them with a fistful of prospectuses (Put Your Money In).
Leaving the saloon, the bookish Foswell agrees to tutor Dick in English and grammar while Dick offers to improve Foswell's street smarts and marketability After they part, Dick notices a "Room For Rent" sign outside Mrs. Mooney's boarding house and is entertained by her sales pitch so he takes it (The Room). A deal is struck, and now Dick has a job, a room of his own, a bath that "best of all is down the hall, not down the street," a start toward being respectable (reprise of Respectable).
Several weeks later Dick is on his way to open his first bank account. Foswell is with him, improvising an English lesson as they walk. Foswell insists that a proper education is the only way to be part of an "up to date and modern" America. They stop to join Snobden and passersby who are gazing up at the large red and gold sign that proclaims "F.W.Woolworth's Emporium" (Keeping Up With The Times). Although it might be major competition for his shop, Snobden reminds Dick that "it's sometimes an advantage to be small." As the number moves to the bank entrance, Allen Carlisle, the President of the bank, joins to affirm one of Alger's theories, that "saving each little sum is the way to go from rags to riches, young man." Dick leaves the bank with his new bank book.
In her room, Stacia and Gerrish argue about their future. He reminds her of their romantic past and assures her that their future will be bright. He has plans. As he weaves his spell, once again she is hopeful for she wants to believe it might all be true; maybe tomorrow. She moves into his arms (reprise of Maybe Today).
Back at Snobden's store, Chapin and Higgins watch Dick joyfully go about his menial duties. The new office boy has become Snobden's pet, continues to show them up, and he must be gotten rid of (A Hardworking Boy). But they need a "wicked little plot." Just then, to Dick's unhappy surprise, Gerrish enters the store, and they argue. Allen Carlisle has also arrived with his small son, Rob. Carlisle remembers Dick and is introduced to Gerrish. Clearly opposites, Carlisle nonetheless offers Gerrish work at his home. Gerrish leaves, saying he will come, but we know he won't.
It is now July 4th, America's centennial celebration at Union Square. Joining Carlisle, Dick is chaperoning Rob at the festivities. Foswell, Mickey Maguire, Snobden, Higgins, Mrs. Mooney and the entire company are there as well (Look How Far We'be Come). In the crowd and confusion of the celebration, Dick does not spot the lurking Gerrish who has used the naI've Stacia to distract Carlisle and pays Mickey Maguire to distract Dick by pick-pocketing his bank book. With Rob suddenly alone, Gerrish snatches the frightened little boy as the sky lights up with fireworks, the music soars and the crowd continues to celebrate. A horrified Dick finds Rob's cap on the ground as the curtain falls.
Carlisle, Dick and everyone in the neighborhood have fanned out to find the missing Rob (Find That Boy!). Carlisle holds Dick responsible for Rob's kidnapping.
Two days later, taking advantage of Dick's plight, Higgins and Chapin have hatched a plot to additionally discredit him (reprise of A Hardworking Boy). Higgins has been locked in Snobden's store to spend the night. The plan: to ransack the shop and unlock the door from the inside. Higgins and Chapin can claim they found it that way in the morning. Since only Dick, other than Snobden himself, has a key, he will be accused of forgetting to lock the door the night before. It doesn't help that Dick is mentioned in the news articles about the kidnapping. Snobden has no choice but to fire him. As Chapin and Higgins gloat, an angry Dick finds himself back on the street, a bootblack once again (reprise of Shine).
In Stacia's room, where Rob is being held, Stacia is confused and frightened. She hadn't known what Gerrish had planned at Union Square. She tries to convince him to return the boy, but Gerrish once again tries to charm her into believing that life will be grand after the ransom is paid (From Now On). This time she resists, and Gerrish leaves angrily to deliver a ransom note.
Mrs. McHugh, the landlady, comes with fresh linens and to remove Rob's lunch tray. Already unhappy with Gerrish being in residence, she has now been told that Rob is Stacia's visiting nephew. When taking the tray she absent-mindedly pockets the colorful handkerchief that Dick gave Rob during the celebration. Alone with the sleepy boy, Stacia puts him to bed (reprise of Maybe Today) and comes to a sudden conclusion.
Back on Wall Street with his bootblack box, Dick is taunted by Mickey Maguire and they fight. Foswell breaks up the fight and comforts Dick, even though he'd been hurt by the standup on the 4th of July. As he leaves to help search for the missing Rob, he reminds Dick they are still partners. Gerrish shows up and discovers Dick is now jobless, almost friendless, bruised and cut from his fight with Mickey. Gerrish tempts him again with his "Cock and Bull" philosophy: in order to survive Dick will have to be more like him. Left alone, examining the broken pocket watch left to him by his real father, Dick vows that will never happen (Yes!).
On the front stoop of her rooming house, Mooney and some of her neighbors, including a tardy Mrs.McHugh, are enjoying their nightly treat of beer (A Handful o' Hops). As Dick and Foswell enter, Dick is shocked to see Mrs. McHugh wiping her forehead with his lost handkerchief. When he learns that it belongs to the "nephew" of one of her tenants, Dick rushes off. Foswell, confused as is everyone else, follows at once.
Meanwhile, Stacia has decided to return Rob to his father. Opening the door to leave, they find Gerrish standing there, having unexpectedly returned for Rob's ring, which he wants to include in his ransom note. He realizes what she's doing and knocks her to the floor. With the door still open Dick rushes in and confronts him, telling him the police are on their way. Angry and frightened, Gerrish fires his pistol and Dick falls to the floor. Terrified, Rob begins to scream. Foswell appears in time to see Dick shot, but he is quickly followed by a policeman who secures Gerrish before he can fire again.
To everyone's amazement, Dick rises unhurt. As Gerrish is cuffed, he asks how Dick survived the bullet, but is led away before he reveals the surprising answer to Rob and Foswell.
Several days later everyone is en route to Carlisle's mansion for a grand party celebrating Rob's return (North of 14th Street). Everyone except Chapin and Higgins, whose scheme to ruin Dick was awkwardly discovered. Even Stacia, in her "very first gown," is going, met and escorted in by an adoring Carlisle. Snobden announces to Foswell that Dick has accepted the chief clerk job at the store on condition that Foswell accepts Higgins old job. It is agreed. Afterwards, Snobden and Mrs. Mooney are introduced, with obvious sparks.
Dick appears dressed in the suit from the store window, the one he first coveted. Foswell runs in from the library where he has discovered a bookblack box. He shows it to Dick. On the side are the words, "Allen Carlisle, Bootblack." With the shoeshine box in hand, Dick ponders his future. He is now a young man on his way to fame and fortune (reprise of Yes!).