William Earl Webb was born in White County, Tennessee, on September 17, 1897. His family moved to Bon Air and then Ravenscroft, where he worked in the coal mines and played baseball for local teams. He began in the minor leagues in 1921 and switched from pitching to the outfield. In the major leagues, he played with five teams between 1925 and 1933. In 1931, while with the Boston Red Sox, the left-handed batter hit 67 doubles, setting a longstanding single-season record.