"The First Lady of Song," Ella Fitzgerald was arguably the finest female jazz singer of all time (although some may vote for Sarah Vaughan or Billie Holiday). Blessed with a beautiful voice and a wide range, Fitzgerald could outswing anyone, was a brilliant scat singer, and had near-perfect elocution; one could always understand the words she sang. The one fault was that, since she always sounded so happy to be singing, Fitzgerald did not always dig below the surface of the lyrics she interpreted and she even made a downbeat song such as "Love for Sale" sound joyous. However, when one evaluates her career on a whole, there is simply no one else in her class.
One could never guess from her singing that Ella Fitzgerald's early days were as grim as Billie Holiday's. Growing up in poverty, Fitzgerald was literally homeless for the year before she got her big break. In 1934, she appeared at the Apollo Theater in Harlem, winning an amateur contest by singing "Judy" in the style of her idol, Connee Boswell. After a short stint with Tiny Bradshaw, Fitzgerald was brought to the attention of Chick Webb by Benny Carter (who was in the audience at the Apollo). Webb, who was not impressed by the 17-year-old's appearance, was reluctantly persuaded to let her sing with his orchestra on a one-nighter. She went over well and soon the drummer recognized her commercial potential. Starting in 1935, Fitzgerald began recording with Webb's Orchestra, and by 1937 over half of the band's selections featured her voice. "A-Tisket, A-Tasket" became a huge hit in 1938 and "Undecided" soon followed. During this era, Fitzgerald was essentially a pop/swing singer who was best on ballads while her medium-tempo performances were generally juvenile novelties. She already had a beautiful voice but did not improvise or scat much; that would develop later.