Webb's mainstay was clearly Broadway theatre. Between 1913 and 1947, the tall, slender performer with the clear, gentle tenor appeared in 23 Broadway shows, starting with major supporting roles and quickly progressing to leads. He introduced Irving Berlin's "Easter Parade" and George and Ira Gershwin's "I've Got a Crush on You" in "Treasure Girl" in 1928; Arthur Schwartz and Howard Dietz's "I Guess I'll Have to Change My Plan" in "The Little Show" in 1929; "Louisiana Hayride" in "Flying Colors" in 1932; and Irving Berlin's "Not for All the Rice in China" in the very successful revue "As Thousands Cheer". His steamy duet with Libby Holman of Moanin' Low stunned the crowd nightly. in 1933. One of his stage sketches, performed with co-star Fred Allen, was filmed by Vitaphone as a short subject entitled "The Still Alarm" in 1930. Allen's experiences while working with Webb in the film appear in Allen's memoirs.