Five O' Henry stories, each separate. The primary one from the critic's acclaim was "The Cop and the Anthem". Soapy tells fellow bum Horace that he is going to get arrested so he can spend the winter in a nice jail cell. He fails. He can't even accost a woman; she (Marilyn Monroe) turns out to be a streetwalker. The other stories are "The Clarion Call" (Robertson, Widmark); "The Last Leaf" (Baxter, Peters, Ratoff), "The Ransom of Red Chief" (Allen, Levant, Aaker), and "The Gift of the Magi" (Crain, Granger).

While standing in his study, author John Steinbeck states that writer William Sidney Porter, who was known as O. Henry, created many lively characters and noteworthy stories, which were often set in turn-of-the-century New York City. Steinbeck then notes that one of the best is "The Cop and the Anthem," in which a homeless bum, Soapy Throckmorton, prepares for the rigors of winter: The well-educated but lazy Soapy discusses his situation with his friend, Horace Truesdale, who does not share Soapy's view that three months in the city jail is a fine way to spend the season. Soapy then begins a campaign to get himself arrested, but despite taking a passerby's umbrella, eating a lavish meal and not paying for it and throwing a horseshoe through a window, Soapy is not arrested. He then approaches a young woman on the street while a policeman stands nearby, hoping to get arrested for annoying her, but when the woman turns out to be a prostitute, Soapy quickly covers his actions so that she will not get in trouble. Frustrated, Soapy and Horace seek shelter in a church, and the peaceful surroundings remind Soapy that he grew up privileged and pampered, with dreams of living a fine life. Determined to reform, Soapy leaves, but is arrested for loitering outside the church. Although Soapy pleads with the judge, assuring him that he is a changed man, the judge sentences him to ninety days in jail.
       Back in his study, Steinbeck explains that O. Henry, who learned about jail "the hard way," never felt superior to the people about whom he wrote, and that "The Clarion Call" is a good example of his fairness: Policeman Barney Woods returns to New York City after escorting a counterfeiter to Ft. Leavenworth, and in the police station notices that the only piece of evidence to the brutal murder of a man named Norcross is a gold pencil holder, engraved "Camptown Races 4 July 1901," which was left at the scene of the crime. Casually asking if he can borrow the evidence, Barney does not reveal that he recognizes it, then goes in search of its owner, hardened criminal Johnny Kernan. Johnny, who was Barney's boyhood friend, is delighted when Barney finds him, and states that he is on his way to Chicago. Barney reveals that he is a policeman and that the pencil holder, which was a prize won by them in a singing contest, links Johnny to the murder. Johnny confesses to the killing but caustically reminds Barney that he owes him $1,000, which Johnny leant to him when Barney sustained heavy gambling debts years earlier. Knowing that Barney could not arrest him while he is in debt to him, Johnny dismisses his former friend. Barney spends the afternoon taking out loans and cashing in his insurance, but when he tries to give Johnny $300, Johnny refuses it, saying that Barney must pay him all or nothing. Johnny then taunts Dave Bascom, city editor of The Clarion Call , that he will not be able to catch the Norcross murderer. Downhearted, Barney returns to the police station, where a headline in the newspaper catches his eye and causes him to rush to Bascom's office. Barney then intercepts Johnny in his train compartment and gives him $1,000 before arresting him. As Johnny is escorted off the train, he spots The Clarion Call 's evening headline, which offers a $1,000 reward for information leading to the arrest of the Norcross killer.
       Steinbeck then relates that although O. Henry was born in North Carolina, he loved New York, and one of his stories, "The Last Leaf," is about the artists of Greenwich Village: Joanna Goodwin is heartbroken when her lover, actor Sheldon Sidney, abruptly ends their relationship, and in her grief, she wanders the streets during a snowstorm. Finally, her eccentric, Russian neighbor, painter Behrman, finds her and carries her to the apartment she shares with her sister Susan. Jo is diagnosed with pneumonia, and despite Sue's best efforts, continues to grow worse. Behrman, who is fond of the sisters, sells one of his surrealistic paintings to art dealer Boris Radolf to pay for Jo's prescriptions. Radolf urges his friend to paint in a more realistic style, so that he can sell his work, but Behrman refuses. The doctor tells Sue that Jo apparently has lost the will to live, and one evening, Jo tells Sue that the ivy vine clinging to a wall outside their window has steadily been losing leaves, and she believes it to be a sign that when the last leaf falls, she will die. Behrman, discouraged over his lack of success, gets drunk but nonetheless tries to cheer up the despondent Sue. Determined to help Jo, Behrman spends the night out in a freezing storm, painting a perfect replica of a leaf on the wall. When she awakens, Jo is thrilled to see that the "leaf" is still there, and assures Sue that she will recover fully. The sisters are saddened to discover that Behrman died from exposure during the night, and when Sue deduces that he painted the leaf for Jo, she tells her that someday she will realize what a great artist Behrman was.
       Steinbeck then notes that to O. Henry, "no one was too good to slip, or too bad to climb," and to illustrate his point, he wrote "The Ransom of Red Chief": In the early 1900s, confidence men Sam "Slick" Brown and William Smith are in rural Alabama, where they are trying to raise capital for a phony stock scheme. Over William's objections, Slick suggests that they kidnap a child for ransom, but the genteel city dwellers are overwhelmed when the boy they abduct, J. B. Dorset, proves too wild for them to handle. While awaiting the ransom, William and Slick spend a harrowing twenty-four hours being tormented by J. B., who steals their watches, insists on being called "Red Chief," intimidates them with his pocketknife and "sics" a wild bear on them. Finally, the weary men receive a note from J. B.'s father Ebenezer stating that he will take the boy off their hands for $250. Desperate to be rid of the rascal, Slick and William return him to his parents, along with all of their money. As they race away, before J. B. can catch up with them, William bemoans his black eye and poison ivy rash, but Slick tells him to cheer up, for a confidence man is nothing without confidence.
       In his study, Steinbeck explains that at the turn of the century, certain social leaders declared that there were only four hundred people in New York worth knowing. In rebuttal, O. Henry wrote what has become one of his most famous stories, "The Gift of the Magi": clerk Jim Young and his pregnant wife Della are deeply in love, despite their poverty. On Christmas Eve, Jim and Della joke about the lavish gifts they will give each other, and when Della walks Jim to work, they admire the wares displayed in store windows. Of especial interest to Della is a platinum watch fob that would go perfectly with Jim's heirloom pocket watch, while Jim points out three, elegant silver combs that would look beautiful in Della's long hair. Determined to get the fob for Jim, Della sells her hair to hairdresser Maurice, although when she sees her cropped head in a mirror, she tearfully wonders if Jim will still love her. When Jim arrives home, he is astonished by Della's appearance but assures her that nothing could lessen his love for her. Jim then gives Della her Christmas present, the silver combs, and although her short hair can no longer hold them, she is touched by Jim's thoughtfulness. Della then gives Jim the platinum fob, and he admits that he sold his watch in order to buy her the combs. As the couple then laugh and embrace, they listen to carolers sing about the joys of the season.