A young Fitzgerald, photographed by Carl Van Vechten in 1940
Fitzgerald made her singing debut at age 17 on November 21, 1934, at the Apollo Theater in Harlem, New York. She pulled in a weekly audience at the Apollo and won the opportunity to compete in one of the earliest of its famous “Amateur Nights”. She had originally intended to go on stage and dance, but, intimidated by the Edwards Sisters, a local dance duo, she opted to sing instead in the style of Connee Boswell. She sang Boswell’s “Judy” and “The Object of My Affection”, a song recorded by the Boswell Sisters, and won the first prize of US $25.00.
In January 1935, Fitzgerald won the chance to perform for a week with the Tiny Bradshaw band at the Harlem Opera House.She met drummer and bandleader Chick Webb there. Webb had already hired singer Charlie Linton to work with the band and was, The New York Times later wrote, “reluctant to sign her….because she was gawky and unkempt, a ‘diamond in the rough’.” Webb offered her the opportunity to test with his band when they played a dance at Yale University. She began singing regularly with his orchestra throughout 1935 at Harlem’s Savoy Ballroom. Fitzgerald recorded several hit songs with them, including “Love and Kisses” and “(If You Can’t Sing It) You’ll Have to Swing It (Mr. Paganini)”. But it was her 1938 version of the nursery rhyme, “A-Tisket, A-Tasket”, a song she co-wrote, that brought her wide public acclaim.
Webb died on June 16, 1939, and his band was renamed Ella and her Famous Orchestra with Fitzgerald taking on the role of nominal bandleader. She recorded nearly 150 songs with the orchestra before it broke up in 1942, “the majority of them novelties and disposable pop fluff”.