“My first musical impressions, I guess, were from listening to piano rolls,” Monk once mused. “Everybody had a piano, and they used to play rolls all the time. So I had one, too. That’s all people listened to, mostly piano music.”1 Thelonious began teaching himself as soon as they rolled the old upright into the door. He banged a little, listened for differences between the black and white keys, tried to mimic his father’s two-fisted barrelhouse style, and in no time was picking out melodies he had heard on the radio or hymns his mother sang. But when Barbara decided that at least one of her children would receive formal lessons, that privilege was initially bestowed on big sister Marion. That didn’t surprise Thelonious, who explained years later, “The girls always took [lessons] in those days.”2
Barbara had other plans for her middle child: She envisioned Little Thelonious playing violin, like many of the West Indian boys in the Phipps Houses. But Thelonious had his own agenda. Perhaps inspired by Louis Armstrong, who was all the rage in the late twenties, or maybe his neighbor James “Bubber” Miley, a local hero and star soloist in the Duke Ellington orchestra, Thelonious wanted to play trumpet. Barbara accommodated her son and purchased a used trumpet, probably from a local pawn shop or from a musician in the neighborhood. He loved the instrument, but as Marion recalls, “The music teacher told my mother that he shouldn’t play the trumpet because it was affecting . . . his blowing and he got interested in piano. So my mother said she’d give him piano lessons. But before that he was playing the piano because my father used to be banging around on the piano.”3 Thelonious himself remembered it differently. He once told writer/radio host Russ Wilson, “I started to study trumpet, but the music teacher saw me playing on the piano and he said, ‘You got to take up piano.’ So I took piano.”4
Thelonious was eleven when he began taking piano lessons, although even his formal lessons began informally. He was so fascinated by the piano that he’d stay in the house during his sister’s lesson and study everything she did very carefully, including the notes on the page. “I learned how to read before I took lessons, watching my sister practice her lessons, over her shoulder,” Monk explained many times, in an effort to dispel persistent rumors of his musical illiteracy.5 He also had an excellent ear. According to Marion, Thelonious could “pick up any tune that came along without music. Mother said that if he was going to play he should learn how to play the right way, so the teacher who was teaching me, which I didn’t like piano lessons, he started teaching my brother in my place. So, he took lessons.” Marion, on the other hand, was really interested in playing the saxophone, “but they couldn’t afford to buy a saxophone for me so I didn’t play that.”6
Monk’s teacher was Simon Wolf. He taught a few of the neighborhood kids and was highly regarded among the parents who hired him. He wasn’t cheap; Barbara paid him seventy-five cents for an hour-long lesson.7 An Austrian-born Jew in his late thirties, Wolf was a fine classical pianist but primarily a violinist who had the distinction of studying under Alfred Megerlin, the concertmaster for the New York Philharmonic. He performed occasionally, but by the mid- to late-1920s, teaching had become his main source of income.8 Barbara learned about Simon Wolf through her neighbors, Cyril and Harriette Heath, whose son, Seifield Gordon Heath, had been studying with him. Gordon remembered Mr. Wolf as “a soft-spoken, small, elegant, young Jewish gentleman who wore his hair just a little longer than ordinary.” He was very well-trained, worldly, and “warm but impersonal, conscientious, and correct.”9 Gordon was a conscientious student, constantly working on scales, Ludwig Spohr violin studies, and Baroque pieces assigned by Wolf. But for all of his work, Gordon Heath never garnered the kind of attention Wolf lavished on his neighbor Thelonious.
Just one year older than Heath,10 Thelonious turned out to be one of Mr. Wolf’s best students. One day, Gordon’s father asked Wolf for an honest assessment of his son’s progress. “He works hard,” Wolf confessed, “but I couldn’t say if he has talent.” Cyril Heath was taken aback. He then asked about Thelonious, and Wolf responded, “I don’t think there will be anything I can teach him. He will go beyond me very soon.”11 Gordon remembered spending much of his junior high school years being compared with Thelonious and enduring his father’s sighs of disappointment. Cyril would often say, “This boy—no father—his mother scrubs floors to pay for his music lessons and look at the progress he is making.”12
Simon Wolf was not a jazz musician; he taught Thelonious works by Chopin, Beethoven, Bach, Rachmaninoff, Liszt, and Mozart. Thelonious developed an affinity for Chopin and Rachmaninoff, and he loved to work through some of the most difficult pieces. Wolf was amazed by how quickly Thelonious mastered many pieces, not to mention his curiosity about the piano’s mechanics and his wide range of musical interests. Monk knew how much he impressed Wolf and was not bashful about saying so. “Didn’t have to study hard—used to amaze all the teachers! No one had to make me study. I was gifted, you know—music.”13
Wolf worked with Thelonious intermittently for about two years. By the time he turned thirteen, it was clear to Thelonious and to those around him that jazz was his first love. What Wolf could not teach him, Thelonious learned from the many jazz musicians who lived in the neighborhood. Besides saxophonist Benny Carter (who moved to Harlem after leaving his parents’ house14), his neighbors included pianist Freddy Johnson (who would later work with Benny Carter and Coleman Hawkins15), reed player Russell Procope (who played with Benny Carter, Chick Webb, and eventually Duke Ellington), and the phenomenal trumpet player “Bubber” Miley, a key figure in Ellington’s “Cotton Club” band in the 1920s, before he succumbed to tuberculosis in 1932 at the age of twenty-nine. The neighborhood was full of jazz sounds. When Thelonious was still in grade school, a group calling themselves the Carolina Five used to gather at the home of Percy and Theodosia Maples and hold informal rehearsals. Miley was part of that group, along with several other neighborhood musicians.16 Even Monk’s next-door neighbor, James Harrison, worked as a professional drummer in a dance band throughout the 1930s.17
The local jazz musician who had the greatest impact on Thelonious’s early development, however, was a diminutive black woman named Alberta Simmons. She appears in no jazz dictionary or encyclopedia, and she never recorded. But for a good part of her life, she was able to make a living playing ragtime and stride piano in the tiny speakeasies in the West 30s, on 53rd and Broadway, in Flushing, Queens, and out of town when opportunities came up. Born in Virginia in 1892 (the same year as Barbara Monk), she was barely in her twenties when she started hanging out at James Reese Europe’s Clef Club on West 53rd Street. There she met Eubie Blake, James P. Johnson, and Fats Waller—all pianists who would influence her style. Her career might have taken off, according to her daughter Alberta Webb, but “Things got tough back there in the 20s and she married again. . . . Being a woman, she got sort of sidetracked trying to raise her children. Unfortunately, things did not work out in later years.” For several summers, she had a regular gig at Jack’s Cabaret in Saratoga Springs, which gave her two children, Archie and Alberta, a much-needed respite from the city heat.18
Throughout the 1920s, she earned a little money giving piano lessons—enough, at least, to list “piano teacher” as her primary occupation in those years. During the Great Depression, she continued to teach but to survive she did domestic work.19 Among her students was Thelonious. Simmons and her children lived with her mother, Ida Washington, at 210 West 61st Street, through the 1920s and early 1930s, before moving to 117 West 60th Street, on the east side of Amsterdam. Simmons’s daughter Alberta, only two years younger than Thelonious, had vivid memories of his visits to the Simmons household. Sitting at her pristine brown Horace Waters upright, Simmons would teach him a variety of stride piano techniques and help him develop his left hand. “Thelonious used to come by and get the little rhythms that my mother had, what Fats Waller and them had. He knew about my mom.”20
The church proved to be another critical source of Monk’s musical knowledge. Barbara taught her son a few hymns on the piano, and every once in a while Thelonious would accompany her when she sang at Reverend W. A. Johnson’s church on West 61st Street. Although these performances were few and far between—usually around religious holidays such as Easter or Christmas—they were memorable. When Monk reached his late teens and early 20s, he continued to accompany his mother during these holiday performances, but as soon as the song ended it was his cue to cut out. He wouldn’t stay for the service. Nonetheless he became steeped in the sacred music of the black Baptist tradition. One account claims, dubiously, that Thelonious studied under “Professor” Buster Archer, Union Baptist Church’s legendary organist, but this is unlikely since the church had moved uptown by the time Monk turned twelve.21
In any case Barbara had much to teach. She adored gospel, hymns, and old spirituals, and could be quite a taskmaster when it came to learning the music. Thelonious’s nephew, Thomas Monk, Jr., remembers Easter Sundays when all the children would have to stand before the church and sing hymns with their grandmother. She’d insist on rehearsals: “We’d go to the house and she’d get on the piano. . . . And we’d be singing and she’d tell us, ‘You hit the wrong note. Up, a little up, a little down.’ She was like my uncle [Thelonious]. She was like a musical instructor. I’d say, ‘I know how to sing it, Grandma.’ She’d say, ‘No, no, you got to sing with this, that, more feeling. Bring out the voice.’ And we’d stay there for about two hours.”22
Besides his mother, the most important influence on Monk’s early development as a musician and as a young man wasn’t a person but an institution—the Columbus Hill Neighborhood Center (renamed the Columbus Hill Community Center in 1933). Armed with a $72,000 gift from John D. Rockefeller, Jr., the Children’s Aid Society transformed the old Henrietta Industrial School at 224 West 63rd Street into an elaborate after-school and summer program for children and adults. The stimulus for Rockefeller’s gift grew out of a study of delinquency among black children in New York City, conducted in the fall of 1927 by a joint committee representing several social agencies. The Center, which opened its doors in October of 1928, was not to be another recreation facility but a kind of hub of community social service. It housed, for example, the Columbus Hill Health Center (AICP), the New York City Health Department’s Baby Health Station, the Urban League, the Columbus Hill Day Nursery, the Child Study Association, and the Henrietta Health Center of the Children’s Aid Society.23
It was a true center of social life for black youth in the neighborhood. Within months of its creation, about 150 girls and 320 boys were active in eighteen clubs covering a wide range of activities, including athletics, swimming, homemaking, tap dancing, and orchestra. By March of 1930, over 800 kids participated in the Center’s various programs and clubs, and the staff consisted of twenty-three volunteers and twenty paid workers.24 For the most part, the clubs were segregated by gender. Boys signed up for metal work, carpentry, and photography with Mr. Banner, and many of the girls could be found in Mrs. McIver’s craft classes, where she taught advanced weaving and block printing.25 Within each gender group, kids were divided by age. Theo Wilson remembered three distinct groups—Junior, Intermediate, and Senior—and in his view, Thelonious policed the age boundaries vigilantly. “When I was a Junior he was a Senior,” Wilson mused. “And if I went into the Seniors’ room to play pool, he would come in and take my stick and say I followed him there. And sometimes I would give it to him, or I wouldn’t. And the last word was, I’d take a pool ball, and on the way back I’d give it to him. He was a big guy, and I didn’t belong in there. But I thought, ‘Who the hell is he? He doesn’t run the joint.’ ”26
Thelonious would beg to differ, especially once he became a Senior. But no harsh words were exchanged; both parties knew better. Strict rules of conduct were vigilantly enforced, and fighting or other acts of misbehavior often resulted in a revoked or suspended membership. Despite San Juan Hill’s reputation for violence, incidents of fighting or serious misbehavior were few and far between. Most children genuinely loved and valued the Center and its predominantly black staff. “It was the greatest thing in our lives,” Mavis Swire remembered. “[The staff] had a way of making you feel like you could do great things. You can do more with your life.”27
The Center was so popular, in fact, that when the Children’s Aid Society announced in April of 1930 that it would have to close its doors due to lack of funding, angry residents organized a mass meeting and accused the Children’s Aid Society of racial discrimination. Leaders of the institutions housed in the building vowed to keep the Center going. The Urban League organized a benefit performance of Marc Connelly’s play “The Green Pastures” less than a month after the announcement, committing all the proceeds to the Center. The mobilization succeeded. The closing turned out to be temporary; the freshly painted and newly repaired Center was back in operation within a few weeks.28
For Thelonious, Marion, and Thomas, the Center became their second home. Marion remembered playing indoor games such as dominoes, checkers, ping-pong, as well as outdoor sports such as paddle ball, a miniature form of tennis. Thelonious rarely beat his big sister at paddle ball, but he excelled on the basketball court (though, contrary to popular myth, he never played for his high school basketball team), and he was a shark when it came to billiards and table tennis. “He was good in pool,” Marion remembered. “He could beat everybody shooting pool, playing ping-pong. I think he won the championship with the boys in ping-pong and I won it for the girls, the championship. He was good.”29 Thelonious and Thomas, despite their two-and-a-half-year age difference, played on the same basketball team at the Center, in the “100-pound” division.30
Thelonious’s appreciation for the Center was captured in an essay he wrote for his tenth grade English class. Titled “Stormy Days in the City and Country,” it compared urban and rural lives for boys:
On stormy days [there] is hardly anything you can do in the streets, so mostly everybody [tries] to entertain hisself at home. Some go home and read, some play checkers, etc. But I don’t stay home very much on stormy days because there is a boys’ club near my home called Columbus Hill Community Center. In this club there is a lot of things to entertain boys with such as basketball, pool, ping pong, checkers, craft classes and many other things. This is the way the average city boy spends his time on rainy days because there are boys’ clubs all over the city.
In the country it is different than in the city because there are not any boys clubs around so the boys go home and maybe invite a couple of his friends over and tell stories to each other. If the boy happens to have some game at home he and his friends play with them. A country boy can’t play a game such as basketball because there is hardly any place to play such a game. If it happen [sic] to be such a place as a boys’ club in the country the boys have to travel so far to get there. This shows the life of the city boy and the country boy on stormy days.31
Thelonious never became a regular member of one of the Center’s orchestras, but he did participate in the music program.32 When he was about fifteen or sixteen years old, the Center held a music contest for a scholarship to the Juilliard School of Music. Thelonious entered, evidently played well, but took second place behind his friend Louis Taylor, a thirteen-year-old piano prodigy who lived a few doors down from the Monks at 227 West 63rd Street. Taylor’s father delivered coal for a living and his mother worked as a domestic for a private family, but they nevertheless considered themselves among the “better classes,” owing to their Barbadian origins. Nellie Monk and other members of the family believed that Taylor was chosen over Thelonious only because the administrators of the Center favored West Indians.33 Thelonious did envy the fact that Taylor had large hands. Thomas Monk recalled, “my brother used to sort of get aggravated because he couldn’t stretch like Louis or the other piano players.”34
Taylor was enrolled in the diploma program at Juilliard from 1936 to 1940, where he studied piano under Etta C. Garcia. He also took classes in Juilliard’s Extension Division and Summer School from 1946 to 1948, and he became a music teacher.35 Years later, according to Nellie Monk, on a rainy night in 1958 during one of Monk’s engagements at the Five Spot, Taylor came to the set, heard what Thelonious was doing, and passed a note to his former adversary, through club owner Joe Termini, indicating that Monk had deserved to win the scholarship that day. Monk just shrugged it off: “I’m glad I didn’t go to the conservatory. Probably would’ve ruined me!”36
• • •
Monk’s formal education was somewhat less successful than his informal music learning. As a junior high student, Monk appeared to be curious and engaging, but his grades were average. He graduated from P.S. 141 at the end of the winter term in 1928 and enrolled in junior high school JHS 69 on West 54th Street in the spring of 1929.37 Junior high was no different from his elementary school in that it had a predominantly black student body and an overwhelmingly white teaching staff, except Thelonious and his friends in the West 60s had to travel a few additional blocks to get to school, crossing the great divide: Amsterdam Avenue. Battles with neighborhood white kids along the Avenue were daily occurrences, but Monk had earned a reputation as one of the kids not to mess with.
Contrary to the common lore that Monk “excelled” in mathematics and physics, his grades were never very impressive. During the seventh grade and through the fall of eighth grade at JHS 69, his math scores were successively 65, 47, and 65. In the spring term of eighth grade and fall of ninth grade, his scores rose to a respectable 80 and 75, only to plummet precipitously once he enrolled in Stuyvesant High School. Besides, he essentially failed geography in junior high, with grades ranging from 35 to 57 during the same period. He performed somewhat better in English (65 and 76 at JHS 69), he earned about a B to B+ average in spelling and drawing, and he deservedly scored a 90 for penmanship.38 He proved quite the draftsman; his mother kept some of his junior-high school drawings for many, many years. His niece Jackie remembered seeing “a fine drawing of an old-fashioned iron. Mrs. Monk hung that drawing and others over the sink as long as I could remember.”39 For almost every other subject—physical training, science, and shop—Monk maintained about a C average. The one area in which he consistently excelled was music, earning Bs and As, which was enough for admission to the prestigious Stuyvesant High School. That, and some lobbying by Barbara.
There was no entrance examination for Stuyvesant in those days,40 and Barbara had good reason to send her son there, even though it was very far to the east and south, at 345 East 15th Street. First, Barbara worked a few blocks from the school, as a cleaner at Children’s Court on 137 East 22nd Street. She was always close to her middle child and preferred to have Thelonious closer to her, especially in light of the proliferation of crime and drugs in San Juan Hill. During the early 1930s, San Juan Hill became a leading center of the incipient heroin trade and the target of major federal drug raids.41 Second, the then-all-boys school was one of the best high schools in the city, then as now. Ironically, though it had an outstanding orchestra and band, Thelonious never participated in the school’s music programs, nor did he take any general music classes. There is no evidence that he even auditioned for the orchestra’s highly coveted piano chair. Stuyvesant did not have a jazz band at the time. Some have speculated that Monk was barred from the orchestra because of his race,42 but there were at least two black student members at the time. Solomon Moore, class of ’33, held a cello chair just prior to Monk’s arrival. Moore was also a star on Stuyvesant’s basketball team. Thomas J. Brown, class of ’35, played violin in the orchestra, performed in the school band, ran track, sang in the glee club, and was a leader in the Pan American Society.43
Thelonious appeared committed to school when he first entered Stuyvesant in the spring of 1932. During his first three semesters, he attended classes regularly, missing only 14 out of 285 days, and he was late only six times. He worked hard, especially for a teenaged boy who loved sports, pretty girls, and playing piano—not necessarily in that order. But in spite of his effort—and contrary to legend—Monk did not perform exceedingly well, continuing his junior-high grades. In his first semester he earned a 68 in English, a 67 in French, a 70 in math, and a dismal 40 in chemistry.44 His best subject that semester was “Mechanic Arts,” in which he scored an impressive 86. The following semester (fall 1932), his English grade dropped to a 40, French to 50, and math to 65. By the spring of 1933, although he attended classes regularly, he seems to have stopped trying. He earned “0’s” in physics and French, a 50 in biology, and a surprising 20 in mechanic arts. The one course that seemed to engage him was English. He not only earned a 66, his highest grade that semester, but his English assignments dominated his composition book.
His tenth grade essays reveal his curiosity, skepticism, and wry sense of humor. Characterizing Charles Dickens’s A Tale of Two Cities as essentially a violent conflict between rich and poor, Thelonious noted how the poor people of France were being “killed in a dreadful manner” while the nation’s rulers continued their profligate lifestyle. But even amidst tragedy, Thelonious always found something amusing: The one example he cited from the text told of a young Frenchman who was sentenced by the state to be mutilated and burned alive for not properly honoring a “procession of monks” that had passed a few yards away from him.45 In another assignment, he summarized a newspaper article about a group of University of California scientists who had invented a machine to revive patients whose hearts had stopped. The machine forced oxygen into the lungs, applied heat to the body, and rocked the patient back and forth until her/his heart began to beat. “The theory is,” Monk wrote, “that the steady change in position will cause gravity to send the blood coursing through the veins and will start the heart beating. I think this will help save a lot of lives providing it does what the inventor states.”46 Another, titled “What is the Best Kind of Stove?”, went for awkward deadpan:
Before the gas stove was invented people had to hang their food over the fireplace in pots. Then after a long time of this miserable way of cooking, at last the gas stove was on the market. Of course, when it first came out it costed [sic] a lot of money but finally it was down and mostly everybody had one. And like anything else it had a bad side to it. Sometimes the people would make a mistake and leave on the gas and the result most of the time was death. Then still it was a good stove because it cooks the food quick, you can cook more of the food and it leaves a better taste to the food.
According to those reasons stated above I think a gas stove is the best kind of stove.47
Oh, happy survivors.
• • •
It is often claimed that Monk played on his high school basketball team, but he never participated in any extracurricular activities at Stuyvesant. As soon as the final school bell rang, Monk rushed to the subway and headed for home. The neighborhood was the center of his social universe; here he earned the respect of his peers and developed a few deep and lasting friendships. When he wasn’t playing basketball or ping-pong at the community center, Thelonious would often visit his friend Harold Francis across the street. Like a number of Monk’s friends, Harold was of Caribbean descent; his parents hailed from Barbados. His father, Frederick, was a bit of a curiosity in the neighborhood because he worked as a stableman caring for horses. Harold and Monk had a lot in common. They were the same age and were known around the neighborhood as excellent pianists.48 The pair spent many hours together taking turns playing for each other, sometimes at the Monks’ house, sometimes at the community center. Occasionally they visited Alberta Simmons.
The Monks’ apartment was a popular hangout not only for Harold Francis but for many of the young neighborhood musicians. Barbara’s doors were always open for her children’s friends, and she enjoyed the music they played. Marion remembers those impromptu jam sessions fondly. The kids would pile into the front room and “they’d be playing and the rest of us would be dancing, you know.”49 Like Thelonious, Harold Francis was determined to become a professional musician. He would struggle until 1946, when he got his big break and replaced Ray Tunia as the pianist/arranger for the Ink Spots.50
Thelonious’s longest-lasting friendship began inauspiciously in the summer of 1933, when he was just shy of sixteen. One day, as he was walking down his block on West 63rd Street, he saw a group of kids preparing to jump a boy who was small and slight in stature and about a year younger than Monk. The boy was desperately trying to defend himself when Thelonious intervened. “Leave that kid alone. He didn’t do anything to you.” Monk was calm but firm. When the gang hesitated, Monk made it clear to all that if they continued with the beating, “you’re gonna have to deal with me.”51 Monk possessed the personal clout and reputation as a pugilist to persuade the kids to back off. In no time, Thelonious and the new boy became inseparable. His name was James Smith but everyone called him Sonny. Sonny wasn’t a musician, but he loved music and liked to improvise on the mandolin and piano. Monk came to respect Sonny’s ear, and Sonny became Monk’s biggest advocate.52
When Sonny met Thelonious, he and his family had just moved from a tiny apartment in a Brooklyn brownstone to a tiny apartment in a five-story tenement house at 226 West 62nd Street. At the time, the Smith family consisted of Sonny, his mother, Nellie, and his two sisters—ten-year-old Nellie and eight-year-old Evelyn, who also went by “Skippy.” Tuberculosis and related illnesses ravaged the rest of the family, including Evelyn’s twin sister, who died soon after birth. Altogether, Mrs. Nellie Smith lost five children to “consumption.” She buried her last child, fifteen-year-old Etta, on March 31, 1933.53
The Smiths’ story is similar to that of the Monks. They, too, were part of the Southern migrant stream that settled in New York City during the early to mid-1920s. And like Barbara Monk, Nellie Smith ended up leaving her husband behind in search of a better life for her children. Born in Florida in 1899 to Harry Young and Martha Brooks, Nellie was a mere teenager when she met Elisha Bennett Smith, a tall, handsome, and debonair Pullman porter who hailed from Sumter County, Georgia.54 Even in his old age, Smith’s niece remembered him as “a wonderful physical specimen . . . who loved to dress and loved music.”55 He played a little guitar and piano, but according to family legend he only knew one song. And every chance he got he played that one song, over and over. The son of former slaves, James Riley Smith and Rosa Alger Battle, Elisha grew up alongside very successful and highly motivated siblings. His brother, James Clifton Smith, became a renowned educator and activist in St. Augustine, Florida, and his three sisters, Rosa Bell, Annie Mickens, and Lula, were all well-educated, strikingly beautiful, and famously independent. In fact, Elisha (also known as E.B.) was sort of the rebel in the family. He dropped out of school early on, loved travel and adventure, and had a weakness for pretty women. One of those pretty women, Nellie Young, was twenty-four years his junior. They married some time during World War I, settled in Jacksonville, Florida, and started a family right away. Nellie bore eight children for E.B.—the sixth child, born December 27, 1921, she named after herself. While Nellie raised his children, E.B. spent much of his time traveling up and down the eastern seaboard for the Pullman Company. He never could suppress his wandering spirit or his eye for attractive women. In 1926, Nellie Smith and her eight children left E.B. behind and made the northern trek to New York.56
She first moved in with her sister Elizabeth Bracy, also known as Aunt “Yank.” Recently widowed, Bracy worked as a housekeeper but owned a small home on Atlantic Avenue in Brooklyn. Nellie, too, found work as a domestic, but it took four years before she was able to move out. But by the time they relocated to Albany Avenue about six blocks away, she had lost four of her children to TB and had contracted the disease herself.57 With Etta’s passing, Mrs. Smith and her three surviving children, Sonny, Nellie, and Skippy, packed their belongings and set out for Manhattan. After about a year living at 226 West 62nd Street, Nellie’s health deteriorated to the point where she could no longer work and the family had to go on relief. They were forced to move again to a slightly cheaper place across the street at 237 West 62nd. Much of the burden of caring for the two girls now fell on Sonny’s shoulders.
Thelonious and Sonny became a conspicuous pair at the playground and on the streets. Many of the girls in the neighborhood found them both to be particularly good-looking, and a few developed serious crushes, despite the boys’ reputation for aloofness. A few of the girls, including Sonny’s sister Nellie, used to gather at Monk’s house to hear him play. Nellie remembered, “I was about twelve when I heard him play the piano, and that was at his house. A lot of young girls used to go to his house. His mother would let them in. Of course, a lot of girls had a crush on him. . . . All the teenage girls.”58 Nellie knew better than to expect sixteen-year-old Thelonious to take an interest in a bashful, skinny twelve-year-old. Still, after the couple was married, she recounted a far more romantic story of their first encounter: “I was playing in a playground, and we had heard about each other. One day he passed the playground, and our eyes met, and I knew him, and he knew me. We didn’t speak then, and we didn’t actually meet until six months later. Years later he could tell me what I wore that day.”59 Perhaps, but if Thelonious felt this way, many years would pass before he began to see little Nellie as the beautiful, intelligent, and charming brown-skinned woman with the distinctively high cheekbones and the penetrating eyes.
Meanwhile, Nellie befriended two sisters who lived just across the street, Geraldine and Edith MacMillan. The MacMillan girls, along with their older sister, Millicent Henry, moved in with their aunt Lizzie Brooks, at 238 West 62nd Street, after their mother died in 1932.60 (Their father left when they were quite young, and was not in a position to care for his children.) “Aunt Lizzie,” as she was known to practically everyone in the neighborhood, was the girls’ maternal aunt—their mother’s older sister. She was listed in the census as married, but her husband did not live with her and she supported the entire household on meager wages earned from domestic service. “She was everybody’s aunt,” Geraldine remembered. “Just a little spry lady [and] a real figurehead in the neighborhood.”61 By the time the Smiths moved to the block in 1933, Geraldine had just turned thirteen and Nellie was eleven. They all attended JHS 69 together, and Nellie and Edith became after-school playmates.
At first, Geraldine had no interest in hanging out with her little sister and her new friend. “She wanted me to come and play with them. But I said they were too young. I felt I was so big and grown. . . . She kept telling me, [the Smiths] are nice, you would like them. So then she thought she was really interesting me when she said, ‘They got a cute brother.’ ” Geraldine had heard the buzz around the neighborhood from the other girls, and she agreed that Sonny was very good-looking, but she felt he was hard to approach and a little too cool. Nevertheless, she agreed to join Edith at the Smiths’ house and in no time she and Nellie were best friends. It would be a little while before Geraldine would make Sonny’s acquaintance, and even longer before she met Thelonious. Eventually, Nellie’s “cute brother” began to take notice when Geraldine blossomed into a young woman.62
San Juan Hill was like a small town unto itself; every circle of friends seemed to overlap. While Thelonious and Sonny were still too cool, and too old, to hang out with Nellie and Geraldine, they were tight with Geraldine’s cousin, Charles Stewart, who also lived with Aunt Lizzie. Stewart, a talented trumpet player and fine arranger, started jamming with Thelonious when they both were about fourteen years old (Stewart was just a few months older than Monk). In later years, Monk would praise Stewart’s playing, comparing him with Clifford Brown. Stewart followed in the footsteps of his cousin (Geraldine’s older brother from a different father), Clarence Brereton, who played trumpet and sometimes trombone in Noble Sissle’s Orchestra during the 1930s, and in John Kirby’s Orchestra in the mid-1940s.63
Around 1933, Monk formed his first band with Stewart and another kid from the Columbus Hill Community Center named Morris Simpson. The son of West Indian immigrants, Simpson was a fine drummer who lived a couple doors down from the Center, where his father worked as a janitor. When Morris wasn’t in school, practicing drums, or playing tennis—one of his favorite pastimes—he helped his mother run a little newspaper stand on the corner of West 63rd and Amsterdam.64 The three of them were only fifteen or sixteen, but they managed to land a few gigs in local restaurants and at dances.
There are no surviving descriptions of their music, but whatever it was, the people liked it. Monk: “They used to have what they called rent parties and they used to hire me to play when I was very young. They’d pay you about three dollars, and you’d play all night for ’em. And they’d charge admission to people who would come in and drink. That’s the way some people used to get their rent together, like that.”65 Nellie wasn’t old enough to attend those parties, but she heard stories from Thelonious and her brother. “Sometimes he’d get money, sometimes they’d give him a story and all that.” On a good night, she said, the band could make up to ten or fifteen dollars—quite a sum at the height of the Depression. “It was always crowded. People would buy pig feet dinners and chicken dinners with potato salad, you know, a dollar a plate or fifty cents a plate.” The gigs were intermittent, but when he did get paid he would always give his mother some money and use the rest to keep himself sharp. “He was earning his own money, buying his own clothes,” Nellie remembered. “He was able to buy his shoes with that.”66
The trio made a few dollars competing in “Audition Night” at the Apollo Theater. Launched early 1934, “Audition Night” took place on Mondays, the professional musicians’ night off, and contestants competed for the grand prize of ten dollars. Second, third, and fourth place winners received five, three and two dollars, respectively. “Audition Night” was not the same as the more famous “Amateur Night at the Apollo” hosted by the Harlem personality Ralph Cooper. “Amateur Night” took place on Wednesdays from 11:00 to midnight, starting at the very end of 1934. Famously, unlike all the other competing amateur night competitions throughout Harlem—both the Alhambra and the Harlem Opera House hosted similar competitions in 1934—the Apollo’s “Amateur Night” was broadcast live on the radio.67 Audition Night was a quieter affair. Nellie, Monk’s siblings, and other family members remember the trio bringing home the ten-dollar grand prize pretty regularly. “The three of them,” Marion recalled, “would go up and they won every time they went up, so they barred them from coming up there because they were winning each time.”68 Nellie recalled in an interview that Thelonious won so many times, for five or six weeks the Apollo became a steady source of income. She, too, remembers the management telling him “Don’t come back anymore.”69 Oddly, Monk’s trio’s victories did not lead to bigger things. Just a few years later, women vocalists were touted by the press and/or earned professional gigs as a result of winning Amateur Night contests. Thelma Carpenter, Billie Drew, and Ella Fitzgerald were all “discovered” because of their Amateur Night performances.70 For Monk, by contrast, his legendary victories on the Apollo stage were just that—legendary.
• • •
For three young men with a little money in their pockets, there were many cheap entertainments in New York City during the Depression. Twenty or thirty cents bought a movie ticket at the Loews on 7th Avenue and 124th, or the Proctor or the Orient along 125th Street. The comedy duo Buck and Bubbles performed at the Mt. Morris Theater, and the Odeon had both movies and live acts. When Thelonious could swing it, he shelled out thirty-five to fifty cents to see some of the big bands at the Apollo, the Lafayette, or the Harlem Opera House—led by Earl Hines, Jimmie Lunceford, and Don Redman, among others. It is very likely that he went to see Willie Lewis’s band at the Lafayette in March of 1934.71 Billed as the “year’s greatest musical sensation,” the Lewis band was on its way to Europe for an extended engagement beginning the following month. Some of the buzz surrounding this band had to do with its sensational new pianist, Herman Chittison. Chittison was one of Monk’s favorite pianists, as Monk later acknowledged.72 Handsome, suave, nine years Monk’s senior, the Kentucky-born pianist, like Monk, had been introduced to music through hymns. At four years old, he had been able to play “Trust and Obey,” and he frequently played piano at his family’s church. At Kentucky State Industrial College for Colored Persons (1925–26), he became the pianist and director of the school orchestra. Two years later he hit the road with Zack Whyte and His Chocolate Beau Brummels and went on to work with Stepin Fetchit and Willie Lewis.73 Chittison tended to play a lot of notes and possessed a demonic ability to play fast; Monk tended to play fewer notes and preferred medium tempos. But Chittison’s influence is audible in recordings by the young Monk. Both loved descending runs, and “fills” (punctuation points at the ends of phrases in a tune) that were deliberately bumpy. Chittison had a strong and active left hand, which he used to create little counter-melodies. And like Monk, when Chittison backed a soloist—including a singer—he was never content to simply feed him (or her) chords in the background. He tended to be extraordinarily busy, filling in every conceivable space to the point of competing with the soloist.74 Chittison possessed a strong melodic sense. His improvisations maintained a solid connection to each tune, and he could really swing!
Playing at the Apollo was exciting, but Monk’s trio’s most important gigs were the Friday night dances at the Community Center. The trio wasn’t paid much, but they had a good time and always received an enthusiastic response. Sometimes they played for the fledgling tap dancers and singers in the neighborhood. Thelonious, who was himself a bit of a hoofer, enjoyed playing for tap dancers. One of the young dancers they backed up was Trotyrine Wilson, “Rita” to her friends. Born in South Carolina, she lived at the southern end of San Juan Hill, on West 55th Street. She was Alberta Webb’s occasional dance partner, and they frequently rehearsed their routines at the Center. Petite and attractive, with big brown eyes and a wide sparkling smile, she was a sensation on the dance floor. And she was a triple threat: She sang and played the piano, not to mention the ukulele. “That Trotyrine was something else,” Alberta mused. “She was a beautiful little gal with them feet.”75
Thelonious thought she was beautiful, too, and he was interested in more than her feet. He was still in high school when he began to court Trotyrine in earnest; she was fifteen and Thelonious was going on seventeen. They dated for a while, but as far as Trotyrine was concerned it was nothing serious. In fact, she already held a torch for Thelonious’s baby brother Thomas, who was a year younger than Trotyrine and painfully shy. (Too shy for Trotyrine, alas.) His son, Thomas Monk, Jr., had always heard that his father “was a wallflower. He wasn’t flirtatious; he wasn’t a womanizer. My father was always that way. Handsome guy.”76 Many of the girls in the neighborhood considered Thomas the better-looking Monk brother, though they each had their share of admirers.
While Thelonious was working hard to woo his first official girlfriend, the trio came to an untimely and unexpected end. Indomitable Aunt Lizzie Brooks had never liked the musicians’ life, and she gave her nephew Clarence Brereton a hard time about it. She had her reasons. “Her youngest brother was a minstrel and he used to travel,” observed her niece Geraldine. “He would write home and say how he didn’t get paid, hardship, he had no carfare to come back home. . . . [H]e finally did come home after many situations like that. But he developed tuberculosis and he died. And she was finished with musicians. She thought that was the worst profession anyone could have. So here are my two brothers, both of them want to play horn and go on the road!”77
Aunt Lizzie was determined to keep young Charles Stewart insulated from professional music, and she did everything in her power to monitor his movements. But with four children to care for and the demands of a full-time job, she could not be everywhere. He snuck out of the house to gigs, or came up with some story to cover his tracks. But one day, while the trio was performing at a club on West 61st Street, Aunt Lizzie stormed into the place, grabbed her nephew by the ear, and literally dragged him off the bandstand. That was the end of Charles Stewart’s music career. Thelonious continued to respect Aunt Lizzie, but he never forgave her for that night. Every opportunity he got, he would say to her, “Why did you stop that boy from playing? He would have been great!” She must have heard Monk say this to her many times; she lived to 105.78
All was not lost, however. Monk befriended another outstanding trumpet player named Denzil da Costa Best. Slight, dark-skinned, and soft-spoken, Best lived with his parents and four brothers on East 100th and Second Avenue—to some San Juan Hill residents, a universe away. Like Morris Simpson, Best was West Indian—his family immigrated in 1916, just one year before Denzil was born. His father repaired elevators for a living, but played bass and tuba in his spare time. Denzil began piano lessons at six, but then switched to trumpet against his father’s wishes. He practiced surreptitiously, and after graduating from high school joined Chris Columbus’s band. Once his dad heard him on the radio, all was forgiven.79 Thelonious thought Best was the Second Coming. “[He] was one of the best trumpets I ever heard. He’d outblow everybody in the place.”80 The feeling was mutual. They were kindred spirits, not only because they lived and breathed music, but because they were willing to take chances. Best admired Thelonious for staying true to his own musical vision despite disparaging critics and musicians. “People would call his changes wrong to his face,” Best later explained. “If he hadn’t been so strong in his mind, he might easily have become discouraged, but he always went his own way and wouldn’t change for anything.”81 Monk and Best became life-long friends. In the meantime, he was the perfect substitute for the grounded Charles Stewart.
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Beginning in the fall semester of 1933, his junior year at Stuyvesant, Monk’s interest in his musical education trumped any glimmer of effort in the classroom. He virtually stopped attending class, showing up only sixteen out of ninety-two days and earning 0’s in all of his subjects. He made a half-hearted effort the following semester, but still only managed to make it to school thirty-one out of ninety-eight days. By April of 1934, Barbara was so concerned about Thelonious that she phoned the counselor to talk about her son’s performance. Thelonious was doing so poorly that school officials had already decided to ease him out. It is not entirely accurate to say that Thelonious dropped out of school. Instead, Stuyvesant officials thought it best to transfer him to Haaren High School.82 Located on 10th Avenue between 58th and 59th, Haaren was within walking distance from Monk’s house and it catered to students who had already entered the job market. The school developed a program whereby students were allowed to create a flexible schedule combining work and school, a good thing during the Depression when few young people could afford to concentrate solely on school.83
Yet Thelonious chose not to enroll in Haaren High. Now that he was making a little money with his trio, he saw no reason to finish high school. He was set: Music was his life. Barbara had left North Carolina and separated from her husband in large part for her children’s education, and now Thelonious had dropped out at age sixteen. He continued to live at home, play music, see Trotyrine, hang with friends, and help out with whatever cash he made. If Barbara argued with him about his schooling, there is no record of it. For a young African-American man in Depression-era New York, any income was welcome. And at least he was still at home with her.
But then the Lord called.