Malcolm arrives in Boston looking like a country person without any sense of urban fashion. He lives with his half-sister, Ella, who encourages him to explore the city before tying himself down to a job. Malcolm quickly sees the difference between the pace and lifestyle of Boston and that of Lansing. He also sees a difference between the lifestyle of the middle-class blacks who, like Ella, live in the neighborhood of Roxbury Hill, and that of ghetto blacks, who have less money and live further down the hill. Malcolm is drawn to the latter, objecting to the ways in which the “Hill Negroes” try to imitate white people and glorify their own menial jobs. When Malcolm finally begins to look for a job, he begins frequenting a pool hall and befriends one employee there, Shorty. Shorty, who turns out to be from Lansing as well, works at the hall racking balls and tending tables, but he is also an aspiring saxophonist with contacts all over town. Shorty immediately takes Malcolm under his wing, giving him pocket money and arranging a job for him.
At the Roseland State Ballroom, where all the big bands perform, Malcolm replaces the shoeshine boy, who has just won the local numbers racket, an unofficial lottery played for small amounts of money. The outgoing shoeshine boy trains Malcolm in the basics of the job, which include tending the men’s restroom, passing out towels, selling condoms, and shining shoes. Malcolm soon learns that much of the job’s income actually comes from selling alcohol and marijuana, and acting as a go-between for black pimps and white customers. Malcolm begins to shoot craps, play cards, gamble, drink, smoke, and use drugs. With his earnings, he buys his first zoot suit, a flamboyant outfit fashionable on the street. He also gets his first “conk,” a hairstyle in which one’s hair is chemically straightened and flattened. At parties, Malcolm overcomes his shyness and develops a great passion for dancing. He contrasts the unadventurous dancing done in Michigan with the expressive dancing that goes on at the Boston parties. Malcolm eventually quits his ballroom job and makes his first appearance at the Roseland as a customer.
Ella gets Malcolm a job as a clerk at a drugstore in Roxbury Hill. Malcolm hates the middle-class atmosphere, but one patron named Laura, a studious high school student, stands out from the others. Once his friendship with her develops, Malcolm confesses to Laura his old dream of becoming a lawyer, which she encourages. Laura is an excellent dancer, but she has a protective grandmother, whom she must lie to and fight with in order to go out dancing. The second time Malcolm and Laura go dancing, they compete in a dance-off at the Roseland, winning over the crowd and even the bandleader, the legendary Duke Ellington.
Malcolm attracts the attention of a white woman, Sophia, and dances with her. He takes Laura home and then returns to the Roseland and eventually leaves with Sophia in her convertible. Malcolm soon dumps Laura and begins to date Sophia. Sophia has white boyfriends in addition to Malcolm, but Malcolm keeps her as a status symbol. By dating an attractive white woman who is not a prostitute, Malcolm becomes something of a celebrity at nightclubs and bars. When Ella finds out about Sophia, she disapproves. Malcolm decides to move in with Shorty. Over the next few years, Malcolm hears about Laura’s falling out with her grandmother, her introduction to drugs, and her stint as a prostitute. Looking back, Malcolm blames himself for ruining Laura’s life.
This section shows how Malcolm’s strong criticism of prejudice within the black community develops early in his life. Malcolm finds irony in the quickness of Roxbury Hill blacks to judge each other and inflate their own status in artificial ways. At a young age, Malcolm identifies the hypocrisy of his neighbors’ tendency to judge each other on the basis of age, home ownership, and length of residency in New England, rather than on the basis of individual actions or character. Though “Hill Negroes” arguably have a better quality of life than the many unemployed black residents of Boston, their unwillingness to acknowledge the menial nature of their jobs while they look down at poorer blacks makes them just as snobbish as racist whites. As a bright youth who does not tolerate false pride or self-deception, Malcolm holds the overly judgmental habits of his middle-class neighbors in contempt.
Malcolm’s experience shows that the tendency to deceive oneself is not tied to having money or being of a higher class than others. The conk hairstyle, popular in middle-class and poor neighborhoods alike, represents black self-defacement and loss of identity. The act of conking, which physically forces black hair to resemble white hair, is representative of the way that black people attempt to imitate white society. “I know self-hatred first hand,” claims Malcolm after describing in grim detail the process of straightening his own nappy hair with a powerful lye solution. Like the drinking and gambling in the ghetto and the pride and delusion of Roxbury Hill, Malcolm views the conk as yet another tactic blacks use to distract themselves from the real problems of their exploitation at the hands of white society. Malcolm sees blacks, unwilling to accept their true appearance, doing themselves physical harm in order to make their hair fit a white ideal of beauty. This need to mesh with white society plagues blacks of all classes because the cost of not fitting in to white society is often too great.