In the 1920s, Webb played in eight Broadway shows and made numerous other stage appearances, including vaudeville, and a handful of silent films. The revue "As You Were", with additional songs by Cole Porter, opened at the Central Theatre on January 29, 1920, running 143 performances until May 29, 1920. Webb was busy with films, tours, and an appearance at the London Pavilion in 1921 as Mr. St. Louis in "Fun of the Fayre" and in 1922 in "Phi-Phi" – he did not return to Broadway until 1923. He then played in the musical "Jack and Jill" at the Globe Theatre for 92 performances between March 22 and June 9 of 1923, followed by Lynn Starling's comic play "Meet the Wife", which opened on November 26, 1923, and ran through the summer of 1924. One of the play's leads was 24-year-old Humphrey Bogart.