Malcolm arrives in Roxbury in his mint green, high-water suit, completely out of fashion and clearly from the countryside. Even Ella is embarrassed by him; but, he notes, his funny appearance will later be a fond memory.
Throughout the book, Malcolm will contrast poor blacks from the country and city as being quite different in their ways of thinking, and this is also more light-heartedly reflected in their attire.
Ella is an extremely accommodating host. She fixes Malcolm a room and feeds him heaps of delicious food, which he thoroughly enjoys. She has recently split with her latest husband, but she seems entirely unfazed.
Malcolm admires his half-sister’s boldness. In everything from her cooking style to her marital relations, she is unapologetic about being herself.
On Ella’s advice, Malcolm sets out to explore and get to know Boston. He first walks around her neighborhood, which the residents refer to as “the Hill” or “the Four Hundred.” The locals there look down on the poorer black people in the “town” area of Roxbury, and Malcolm is amazed at their behavior. He mistakenly believes they are more successful than the others, but eventually learns that their snobbery is mostly unfounded.
Within the very layout of the city, Malcolm can see how a particular group of African Americans separate themselves off from others based on economic class. This attitude of superiority is also a reflection of the attitudes of whites towards poorer blacks.
One major marker of class is those who own their own homes, a group which is further subdivided between native New Englanders and Southern and West Indian migrants. The “Four Hundred” people refer to each other as “professionals” even if they are just working as janitors or bootblacks in professional, white offices – a self-delusion Malcolm cannot stand.
The term “professional” acts as an instance of tragic irony, in which the audience (and the other neighbors) knows that they are not real professionals, but the people themselves are caught up in their own delusion.
Malcolm then starts to venture into the rest of Boston. He sees historical monuments, Boston University and Harvard University, and the main train stations. He takes in the sights of all the big restaurants and stores and movie theaters. Malcolm is particularly attracted by the Roseland State Ballroom, where all the major acts come to perform.
This more expansive trip through Boston shows all of the glamor and wealth of a big city, but it also implicitly marks these areas as off-limits to African Americans, who instead stay within Roxbury.
Once his sightseeing time is over, Malcolm starts to spend more and more time in the “ghetto” part of Roxbury, attracted by its excitement. Ella grows concerned, trying to convince him to meet the other kids his age in the area, but Malcolm sees himself as much older than them. Besides, he feels much more at ease in the town area than on the Hill.
Malcolm sees himself as older and so do his peers. This is partially due to his physical stature, but also because of his more mature way of carrying himself. These qualities will make him a natural leader throughout his life.
Malcolm is entranced by all the cool cats who stand around in their fancy suits and with their hair “conked” (chemically relaxed to lie straight). He is overwhelmed by all the slang and gambling rackets going on around him.
For a small-town boy, the hustle and bustle of the big city life is enchanting, and Malcolm similarly attempts to enchant his readers with his descriptions.
Deciding it’s time to get a job (a.k.a a “slave”), Malcolm goes into a poolroom to talk to someone he’s heard of called Shorty. The two soon learn they’re both from Lansing, and Shorty enthusiastically promises to take Malcolm under his wing. He starts to point out who’s who in the pool room, like the drug dealers, pimps, and gamblers. Shorty starts to spread the word to everyone that Malcolm is look for a “slave,” and they promise to look out for openings.
As will happen many times throughout his life, Malcolm encounters someone with whom he immediately forms a bond and who agrees to help him through this new phase in his life. In this case, Shorty is his early teacher in learning about the Roxbury environment. The slang term “slave” is brutally ironic considering the past of black enslavement in America, and the way that economic and institutional racism continues that history of oppression.
Shorty talks about himself, as well. He shows Malcolm his saxophone and tells him that he “plays the numbers” (the lottery) every day, hoping to hit the jackpot and win enough money to put a jazz band together. He also confesses to having an attraction to white prostitutes. Shorty then gives Malcolm a couple dollars and promises to call.
For Malcolm, Shorty’s love for jazz and white women are connected. Many African American musicians survive mostly through performing for white audiences, who then also fetishize those black musicians.
By the time Malcolm gets home, Shorty has already left a message with Ella that a position as a shoe shine boy has opened at the Roseland State Ballroom. In awe at the idea of being near so many famous musicians, Malcolm rushes out.
The new position as shoe shine boy is a metaphorical “first step.” For Ella, it’s a step in the wrong direction, but not according to Malcolm and Shorty.
Malcolm arrives at the ballroom, asking for the shoe shine boy, whose name is Freddie. After taking a quick peak at the beautiful ballroom, he heads upstairs. Freddie, who has just won some money and so will be moving on from his job shoe shining, agrees to show Malcolm the trade so he can take over at the next dance.
Freddie represents exactly what Malcolm would like to achieve. He’s been a successful hustler, and now with a little luck, he’s moving on to better things.
With precision, Freddie lays out the tools of the trade on his stand, and begins to show Malcolm how it’s done. He also teaches Malcolm his first real “hustle”: if Malcolm runs to the guys leaving the bathroom and hands them a towel, Freddie says, they’ll be embarrassed about not washing their hands and give him a tip. The other trick is to “Uncle Tom” (or act in a stereotypically subservient way) to the white customers, who will then tip more.
Malcolm emphasizes to the reader how much skill is involved in even a seemingly simple task like being a successful shoe-shiner. Every step involves impressing or flattering the white customers in a conscious effort to make them tip more.
In between practicing on Freddie’s shoes, Malcolm goes off to watch the dancing. He is enchanted by all of the white patrons, dressed up and carrying large bundles of cash, and by hearing all the Benny Goodman songs performed live.
Even though Malcolm will participate in the African American events here, the wealth and splendor of these white patrons creates a stark contrast to his own life.
After cleaning up the ballroom and while driving Malcolm home, Freddie clues him in on the main “hustles” for a shoe shine boy. He should start to buy condoms and then sell them for profit at the end of the dances, and once he’s experienced, he can move on to selling liquor and marijuana reefers.
As with many things Malcolm will learn about, being a shoe shine boy is not what it appears; instead, there is a complex system operating in the background.
After a few weeks, Malcolm runs into Freddie downtown, and they laugh together. Malcolm has come to realize that the “side hustles” are actually the main source of income. In addition, he’s started to pass on the phone numbers of black prostitutes (for a tip) to white men.
In Malcolm’s life, sex between whites and blacks will often be a complicated and exploitative relationship. This is his first of many encounters with that world.
While most of the events are white only, Roseland’s also brings in black bands for the black community. On these nights, the ballroom is packed, and many of the musicians come to have their shoes shined, including Duke Ellington and Count Basie. Malcolm recounts the time Johnny Hodges forgot to pay him.
Malcolm’s relationships with famous musicians may seem glamorous, but they also imply something else: at the end of the day, African American shoe shiners and musicians both are still simply employees for white people.
At the black dances, the dancers are much more improvisational and loose than the dancers at the all-white events (this may have been influenced by the large amount of alcohol snuck in to the black dances). In the last hour, the band yells “Showtime!” and only the best dancers stay on the floor to compete. With the lights shining and the hall rocking, Malcolm feels electrified.
Malcolm’s genuine love of dancing, music, and the joyous atmosphere of the dance hall complicates the image of him as an austere Muslim preacher. The reader is forced to see Malcolm as a more dynamic character.
Around this time, Malcolm starts to hang out socially with Shorty and his friends, where they play craps, drink, smoke, and tell jokes late into the night. He starts to grow his hair out so that he can “conk” it, and Shorty tells him to buy his first zoot suit (an especially baggy style of suit).
Malcolm then contrasts his positive memories with others that he is now ashamed of. As an older man, drugs, alcohol, and conks all represent a degradation of his self-worth.
At a local neighborhood store and on Shorty’s recommendation, Malcolm gets measured for a sky blue zoot suit that he buys on credit (a practice that Earl Little always condemned). The store manager helps him complete the look with a thin leather belt with his initial L on it, a hat with a feather, and a long gold-chain watch.
Malcolm’s description of his trip to the tailor and his new suit is tongue-in-cheek. To him, what sounded and looked great at the time now just seems ridiculous.
While Ella doesn’t approve of Malcolm’s new attire, she accepts it as inevitable, given the style of the times and his group of friends. Malcolm gets photos taken of himself in his new attire, and sends one copy to his siblings, gives one to Ella, and one to Shorty, who is noticeably moved by the gesture.
Shorty and Ella are the two most important people in Malcolm’s life now. Even though their opinions may differ, Malcolm values them both.
Finally, Malcolm’s hair is long enough to be conked for the first time. He and Shorty go to the drugstore to buy the ingredients for a do-it-yourself conk, and then head to Shorty’s apartment. Shorty mixes the concoction, telling Malcolm that the lye will burn his scalp badly, but that it’s necessary to make his hair stay straight.
This is an important step for Malcolm to take into fitting into the local community of hustlers. But hustlers are always fighting for cash, and Malcolm’s DIY conk testifies to that life of struggle and hardship.
At first the chemicals just feel warm, but then Malcolm begins to feel like his head is on fire. After withstanding as long as he can, Malcolm rushes to wash out the lye. Shorty helps him to get all of the relaxant out, dries him off, and shows him his brand new conk. Malcolm’s reddish hair now lies straight across his head.
The process is a very literal baptism by “fire.” After enduring as much as he can and passing through the flames, Malcolm (who fittingly has naturally red hair) emerges as a new man.
Malcolm is in love with his new hair and vows to never go without a conk again. He reflects later that this was his first “step towards self-degradation,” as he attempted to look white by enduring so much pain just to have straight hair. He observes that both lower class black men and upper class entertainers conk their hair, and he admires those who have chosen not to do so. Malcolm sees it as a symbol of shame, both for himself and for others who get conks.
In his strongest language yet, Malcolm attacks one of the symbols of how racism has dug deep into the African American psychology of the time. He offers himself as an example of someone who has also been affected by those illusions, showing that he understands other victims as well.