A diminutive man, who suffered from tuberculosis of the spine, which made him hunchbacked and prone to spells of hospitalisation before his early death, Webb was one of the most talented drummers of the swing era, as well as the highly successful leader of New York's most popular big bands.
Webb was famous among his contemporaries for memorising every detail of an arrangement, which meant that his drum accompaniments would always fit the written chart to perfection. He first moved to New York from his native Baltimore at the age of sixteen, and before long was leading his first band.
By 1927 he was playing major venues such as the Savoy in Harlem, which was to become the band's home for much of the 1930s, and where he built up a formidable reputation with listeners and dancers alike. From 1933, he was resident at the Savoy for a large part of every year, playing lively charts by altoist Edgar Sampson, that featured trumpeter Taft Jordan, trombonist Sandy Williams, and a succession of reed soloists including Louis Jordan, not to mention Webb's own flamboyant drumming.
The band made many successful recordings, and then in 1935, scored a major coup by taking on the then unknown Ella Fitzgerald as vocalist. She had a series of hits including A-Tisket A-Tasket in 1938, and eventually went on to take over the band when Webb died. He was much mourned, especially among his fellow drummers, among whom he had become a legendary figure for his ability to win 'cutting contests' against other musicians.
He famously battled the Benny Goodman orchestra, taking on its drummer Gene Krupa. In the opinion of his Harlem audience, Webb won virtually all these battles in style, with tremendous spirit and flair for a man who for much of his life overcame illness so successfully.