Introduced to the Harlem Stride piano style that would be his signature by jazz legend James P. Johnson, Fats Waller would become a master of satirical piano compositions and a comedic performance style. Waller began performing at age ten in school concerts and in his father's Harlem church. Although encouraged to become a classical pianist by his father, Waller forged his own path after meeting James P. Johnson. By the early 1920s Waller's reputation began to spread around Harlem music circles and he became a noted keyboard player in cabarets and nightclubs, accompanying greats including Bessie Smith and Alberta Hunter. In 1922 he recorded his first song, Muscle Shoals Blues/Birmingham Blues with Okeh Records.

In addition to making his mark as a performer, Waller was a renowned songwriter. He sold his first song, Squeeze Me, in 1923 and by the end of the decade his songs were being performed and recorded by Fletcher Henderson and Cab Calloway. He and Andy Razaf wrote most of the score for the Broadway musical Keep Shufflin' in 1928; the two would collaborate again on the music for Connie's Hot Chocolates in 1929. Between 1929 and 1934 Waller recorded a string of piano pieces including Handful of Keys, Smashing thirds, Numb Fumblin', Valentine Stomp, Viper's Drag, Alligator Crawl, and Clothes Line Ballet. In 1936 he started a sextet called Fats Waller and His Rhythm. The band recorded several hits including I'm Gonna Sit Right Down and Write Myself a Letter, Lulu's Back in Town, and Your Feet's Too Big. He performed regularly on radio and toured before sell-out crowds in the United States and in Europe. Thirty five years after his death, Waller's legacy was exhumed through the Broadway musical Ain't Misbehavin', starring Nell Carter and directed by Richard Maltby. A revue of Waller songs, Ain't Misbehavin' won three Tony Awards, including best musical, and sparked a resurgence in the popularity of Waller's music. After Ain't Misbehavin' several of his long unavailable recordings were reissued.¹⁰⁹