Lester's gloomy stage persona was seen to its quintessential comic effect in the long-running musical The Arcadians (1909) in which he delivered optimistic lyrics in a lugubrious manner.
[3] He was booked for further monologues and sketches by Butt, and in 1906 he appeared at the Gaiety Theatre in London as the Lost Constable in George Grossmith Jr.'s musical The New Aladdin, in which the reviewer in The Times judged his performance the funniest thing in the show.
In a cast that included Phyllis Dare, Dan Rolyat and Florence Smithson, he was singled out by The Times, which found him "more hilariously melancholy than ever: the audience rocked to hear him sing that his motto was 'always merry and bright.
"[3] In May 1915 Lester reprised his original role in a revival of The Arcadians, and among his most celebrated shows of the First World War years was a revue, The Bing Boys Are Here (1916) in which he and George Robey co-starred with Violet Lorraine.
[8] His later roles in musical comedy were Umpicof in Round the Map (1917), Hu-Du in Shanghai (1918), George in The Eclipse (1919) and Miggles in a revival of The Shop Girl (1920).