Rothenstein produced several drawings of Pinero in the 1890s, one of which appeared as a lithograph in his book of English Portraits (1897). The playwright and the painter were well acquainted; Rothenstein attended the opening night of Pinero’s Trelawny of the 'Wells; in 1898, resulting in a study of Irene Vanbrugh in the role of Rose Trelawny (illustrated in The Graphic, 1910). Other contemporary actors, including Ellen Terry and George Bernard Shaw, sat for Rothenstein, whose interest in the theatre was strengthened by his marriage to Alice Knewstub, an actress who went by the stage name Alice Kingsley.