Penley began his stage career in 1871 in farce and was soon performing in musical theatre. From 1875, he appeared in several runs of "Trial by Jury", making an impression when he became a replacement in the role of the Foreman of the Jury. Over the next decade, he steadily gained prominence in character roles in operettas and Victorian burlesque, playing in several of these at the Royal Strand Theatre and other London theatres. In 1879 he toured as the leading comic role of Sir Joseph Porter in "H.M.S. Pinafore" and in 1880 he visited the US in a tour.