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Entrepreneur Ed Smalls owned a small venue in Harlem, the Sugar Cane Club, from 1917 to 1925, which catered primarily to residents. When Smalls opened Smalls Paradise, he arranged a lavish gala for the club's opening, which almost 1,500 people attended. At the time of the Harlem Renaissance, Smalls Paradise was a well-known black-owned and integrated nightclub. They were in the basement of 2294 Adam Clayton Powell Jr. Boulevard at 134th Street.
Opening Day jazz music was by Charlie Johnson and his musicians, who remained the "house band" for ten years. The members of Johnson's band included Jabbo Smith, Benny Carter, Jimmy Harrison, Sidney De Paris, and Sidney Bechet. The entertainment at Smalls Paradise included servers dancing the Charleston or roller-skating as they delivered customer orders. Servers were also known to vocalize during the club's floor shows. Smalls was open all night, offering a breakfast dance that featured an entire floor show beginning at 6 a.m.
In the early 1930s, Smalls hosted Billie Holiday's first audition as a professional singer. A young Malcolm X worked there as a waiter between 1942 and 1943. W. E. B. Du Bois celebrated his 83rd birthday at Smalls Paradise on February 23, 1951. The banquet, sponsored by Albert Einstein, Mary McLeod Bethune, Paul Robeson, and others, was originally to be held at New York's Essex House. This was during the era of the House Un-American Activities Committee; a pro-McCarthy group circulated a newsletter labeling Du Bois, Einstein, and others connected with the dinner as being pro-Communist. When the Essex House canceled the banquet, Smalls Paradise stepped in. Ed Smalls sold the club to popular disc jockey Tommy Smalls in late 1955.
By the late 1950s, the club had lost substantial business. Basketball player Wilt Chamberlain purchased it with business partner Pete McDougall in 1961. Chamberlain also began booking black comedians; Redd Foxx played there. He renamed the venue Big Wilt's Smalls Paradise and changed the club's style of music from jazz to rhythm and blues for economic reasons. Ray Charles was one of the first performers at Big Wilt's Smalls Paradise.
By the early 1970s, revamping Big Wilt's Smalls Paradise was necessary again. Some club patrons used the night spot for illicit activities like drug dealing. The Abyssinian Development Corporation purchased the structure. The nonprofit corporation, affiliated with the Abyssinian Baptist Church, planned to renovate the building and add three floors to it completely. Further plans for the building were to lease the structure for 50 years to the New York Board of Education to house its Thurgood Marshall Academy. The school opened in 2004, ending Smalls Paradise.