He alternated between band tours and residencies at New York City clubs through the late 1920s. In 1931, his band became the house band at the Savoy Ballroom. He became one of the best-regarded bandleaders and drummers of the new "swing" style. Drummer Buddy Rich cited Webb's powerful technique and virtuoso performances as heavily influential on his own drumming, and even referred to Webb as "the daddy of them all". Webb was unable to read music, and instead memorized the arrangements played by the band and conducted from a platform in the center. He used custom-made pedals, goose-neck cymbal holders, a 28-inch bass drum and other percussion instruments. Although his band was not as influential and revered in the long term, it was feared in the battle of the bands.The Savoy often featured "Battle of the Bands" where Webb's band would compete with other top bands (such as the Benny Goodman Orchestra or the Count Basie Orchestra) from opposing bandstands. By the end of the night's battles the dancers seemed always to have voted Chick's band as the best. As a result Webb was deemed the most worthy recipient to be crowned the first "King of Swing". Notably, Webb lost to Duke Ellington in 1937. Although a judge declared Webb's band the official winner in 1938 over Count Basie's, and Basie himself said he was just relieved to come away from the contest without embarrassing himself, surviving musicians continued to dispute the ruling for decades to follow.