The narrator pauses his story to describe the Club in more detail since he spends so much time there. In the basement is a Chinese restaurant, and many Club patrons have discovered that Chop Suey is good for soaking up alcohol. On the main floor are a parlor which opens into a back room, which is covered from ceiling to floor with pictures of notable African Americans. There is also a private room for parties and an open space for performers. The narrator describes the performance spaces as "a center of colored Bohemians and sports". Many notable personalities wander through its rooms. Admirers of both races visit frequently. Meanwhile, the wealthier Club patrons think nothing of buying champagne for everyone in the room.
The narrator describes the few white patrons who come to the Club. Some stay a few minutes, others remain the whole night. Some actors come to see how "colored" people act so they can work on perfecting their own "darky characters" (78). There are also a few women who appear to be white who come to the Club with dark-skinned companions. One of them in particular catches the narrator's eye. He nicknames her "the widow", because rumor has it that she inherited a large sum from a late husband. She is cultured and well-traveled, and pays for her young African American companion to wear fine suits and travel in taxicabs. The morning after the narrator's first eye-opening night in New York City, he and his friends put off finding jobs and instead return to the gambling house to get into good spirits. The narrator loses fifty dollars but is optimistic that he will regain his luck next time. At the Club, the narrator tries to play ragtime like the resident pianist, but finds the task more difficult than he had expected.
Eventually, the narrator takes a job rolling cigars to make money during the day and gambling it away at night. He falls into a routine going to the craps table and afterwards, whether he wins or loses, he spends time at the Club. Soon, he decides to gamble full-time and gives up his steady cigar-rolling work. For the next year, which the narrator describes as a "dark period", he many other bright ambitious types become obsessed with the world of gambling and glittering nightlife. Sometimes he has money, sometimes he does not. However, during this year he does manage to master ragtime and becomes a popular entertainer at The Club. He soon earns the nickname "the professor" and starts making a living playing the piano, which weans him off his gambling habit. It is through his talent for ragtime that the narrator will have the opportunity to explore the world.
One night, a young white man (whom the narrator later refers to as "the millionaire), impeccably dressed and very cultured in appearance, comes into the club and, week after week, gives the narrator five dollars after each of his performances. He mysteriously asks the narrator to fill an engagement for him, giving him no other information than a visiting card. On the night of the "engagement", the narrator arrives at the millionaire's house to furnish musical entertainment for a dinner party. The lavishly furnished house is comfortable but elegant, and the guests cultured and vibrant. While the narrator plays classical music, a background score, he observes the guests around him, noting the lovely women as well as the millionaire, whose reserve grows in proportion to the guests' gregariousness. The narrator soon learns that this is simply the way the millionaire always behaves at social events.
When it is time for dinner, the millionaire encourages the narrator decides to switch to ragtime music. His performance delights the guests and they flock around the piano, nearly forgetting about their food. The millionaire compliments the narrator when the guests leave and tells him that he will give him lots of work as long as he does not perform for any other private employers. The narrator readily consents. The narrator begins playing regularly for the millionaire. What is striking, the narrator observes, is that the millionaire's love for music is all-consuming and his "powers of endurance in listening often exceeded [the narrator's] in performing". The narrator's arms often grow sore and his mind fatigued, playing for hours while the millionaire listens quietly with his own eyes barely open. Over time, their relationship grows warm and familiar.
The narrator still headquarters at the club, playing for fun. He attracts the attention of many women, including the widow. He is warned that her younger African American companion is violent and hot-headed, evidenced by the lovers' frequent quarrels. However, the widow is so beautiful that the narrator cannot help but be charmed by her. One night, she asks him to have a drink with her and he agrees. Mid-conversation, the narrator becomes aware that her companion has arrived. The widow's companion approaches their table and just when the narrator thinks he is going to strike her, the widow's companion pulls out a revolver and shoots her in the throat. The narrator leaps up and runs frantically into the city streets, frightened and paranoid, until the millionaire drives by and finds him. The narrator tells him what has happened and the millionaire replies, "'I decided last night that I'd go to Europe tomorrow. I think I'll take you along instead of Walter'" (91). The narrator agrees to this and sits back in the car; he comments, "the jet of blood pulsing from [the woman's throat] had placed an indelible red stain on my memory".
The journey to Europe is difficult for the narrator at first; he is seasick and afraid that he will somehow be tied to the murder. He eventually feels better and by the time they arrive in Paris, he is excited for his next adventure. He writes that "there was awakened in my heart a love for France". He details his sightseeing and his love of Parisian culture. The millionaire never treats him as a subordinate, but as an equal. During the days when the millionaire is occupied, the narrator wanders around Paris and begins learning French. He devotes himself to refreshing his Spanish and learning German as well. He spends many evenings at the Opera, and one night, he notices a striking young girl in the audience. She is with her parents, and when the narrator looks a bit more closely, he notices that man is his own father, meaning that the girl is his sister. He leaves the building, feeling suffocated and miserable. He cannot decide whether he wants to weep or curse.
The millionaire decides he is tired of Paris, and the narrator is saddened to have to leave. They move on to London, which the narrator finds distasteful at first. He soon grows to love it, though, for different reasons than he loved Paris. They make a stop in Amsterdam and then move on to Germany. In Berlin, the narrator meets some of the millionaire's friends who are also musicians. One night, when the millionaire is entertaining these men, he asks the narrator to play ragtime. The narrator complies, and before he can be commended, a large German man takes over the piano to play many variations on the the ragtime tune, in several different musical genres. The narrator is astonished, for "this man has taken ragtime and made it classic". The narrator then loses interest in his travels. He wants to move back to the South, live among African Americans and feel the inspiration firsthand, but he is nervous to leave the millionaire. They are friends and the narrator knows how much music means to the millionaire.
When the millionaire announces his plans to go to Egypt and Japan, the narrator finally reveals his plans to return to the USA and pursue a career in music. The millionaire wonders why he would want throw his life away with the poor and ignorant "colored" people in America when he can pass for white. They have a deep discussion about race, leading the narrator to conclude that the millionaire does not feel prejudice but is aware that prejudice exists. The millionaire's perspective is this: "I can imagine no more dissatisfied human being than an educated, cultured, and refined colored man in the United States". He believes that life should be enjoyed that it is a waste of time attempt to ease the world's suffering.
The narrator admits that the millionaire's ideas are compelling and wonders if his motivation is to help his own people or to find success for himself. He concludes that there is some selfishness in his ambitions, as he will be more remarkable as a "colored composer" than as a white one, but that he also feels "stirred by an unselfish desire to voice all the joys and sorrows, the hopes and ambitions, of the American Negro, in classic musical form". The millionaire accepts the narrator's decision and gives him a large sum of money, with a promise of more should he need it. The narrator does not know if the coldness of their parting is because the millionaire feels that the narrator is making mistake or because he is trying to cover up his own emotions. The narrator soon boards a ship to Boston, and journeys back to his home country.
In these chapters, the narrator establishes himself in New York and unearths new facets of his personality, first as a gambler and then as a the millionaire’s personal musician. Although he gets off to a shaky start with ragtime, he soon becomes the best ragtime player in the city, noting that ragtime opens doors for him that his study of Chopin and Mendelssohn never could. His time in New York ends abruptly, though, when has a run-in with the widow's kept man and witnesses her violent death at her companion's hands. However, after his jaunt in Europe, it is music that compels him to come back to the states, just as it catalyzed his departure.
As the narrator travels from place to place in the United States, his story reveals that the physical and psychological barriers between the races are invisible and complex. Critic Kathleen Pfeiffer writes, “the Ex-Colored Man’s embodiment of physical whiteness and legal blackness literalizes the instability of these ideological frontiers, and demonstrates that their barriers are increasingly permeable.” The narrator never ascribes to fixed boundaries, even as a child. He resists music lessons that curtail his creativity and is unimpressed by great books, including the Bible. He evinces frustration that these books present history in a fragmented, impersonal way. His journey of discovery, as described in the novel, is a layered narrative that reveals the history of racial identity in America with all its inexplicable contradictions.
However, as Pfeiffer points out, the narrator still has an overwhelming impulse to order and categorize. He lists the content of each of his childhood rooms, compares and contrasts European people, and develops categories of "colored people" in the South, Club patrons, and gamblers. Despite this, Johnson denies his reader the same ability to find order in his narrative, as he liberally jumps back-and-forth chronologically, defies literary conventions, and mixes genres. It is difficult to read Autobiography through any single lens or categorize it neatly. Just as the narrator vacillates between "passing" as white or embracing his blackness, his internal loyalties fluctuate as well. This could be a symptom of his racial self-hatred, or indicative of a unique form of self-determination; Pfeiffer writes, “neither wholly black nor wholly white, the Ex-Colored Man believes himself to be free from the politics which race loyalty demands.”
The narrator is extremely adaptable in all of his jobs and locales, and “his only constant, essential characteristic is that he possesses no constant, essential characteristic.” Johnson even avoids giving the narrator and most of the other characters real names, identifying them by their physical characteristics or jobs. Traditionally, white masters had the authority to name their slaves, but after emancipation, African Americans reclaimed autonomy by un-naming or re-naming themselves. The narrator avoids being controlled by either tradition and creates a system of identification based neither on the slaveowners' tradition or by rebelling against it.
The narrator's ability to straddle racial categories is evident in the novel’s treatment of music. The narrator describes his individualism as a musician, eschewing formal lessons and abhorring the role of an accompanist. He distinguishes himself a classical musician, then, in New York, starts employing ragtime techniques to come up with new variations on classical music, and finally, during his stint in Europe, he is inspired by a German musician's classical interpretation of ragtime. Some critics excoriate the narrator for taking an African American form and turning it into something half-white, and then for venturing to exploit music in the South simply because he sees it that route as the most promising. He cannot accept ragtime music for what it is and instead follows the German musician’s lead by adulterating it with classical European music. However, it can also be said that the narrator does not accept classical music for what it is either. This blurring of musical boundaries was a reality of the ragtime phenomenon, with both white and black artists borrowing from each other and achieving success. Also, most of the narrator’s most important moments take place at a piano, which seems to challenge the idea that the narrator’s white identity equals a loss of musical inspiration.