The Little Minister, 1925 Sidewalks of New York, featuring Ruby Keeler, 1927 Waterloo Bridge, 1930 He also produced several musicals and musical reviews during his career, including Watch Your Step, the first musical by Irving Berlin (which featured Vernon and Irene Castle in their Broadway debut). In 1915, Dillingham hired the Russian prima ballerina Anna Pavlova to perform in New York City for six months. Personal life Dillingham was married in 1896 to actress and singer Jennie Yeamans who was a former child star. She died in 1906. On May 5, 1913 in Purchase, New York, he married Eileen Ann Kearney formerly of Stillwater, Minnesota. The new Mrs. Dillingham was part of the Alla Nazimova dance troupe and later was in several productions of Dillingham's. The couple were regulars in society just as the old guard and the theater world began mingling. They were among the early snowbirds fleeing to Palm Beach during the winter season. They were often at European social scenes such as the Ascot and Longchamp racecourses. The marriage broke up in August 1924 after Mrs. Dillingham became enamored of Julius Broome Livingston Allen, twelve years her junior, whom she married in October of that year. The divorce caused a sensation and was reported in Time magazine. Eileen was a life long friend of Florenz Ziegfeld's wife the actress Billie Burke. She died in 1957 after divorcing her second husband, whom she had married twice. There have been various reports and rumors of Dillingham's homosexuality including a longtime relationship with Charles Frohman, with whom he lived for some time between his marriages. His second wife's family believed theirs to be a marriage of convenience. He was a pall bearer at Harry Houdini's funeral where he was thought to have quipped, "Let's see him get out of this one." Ill health and the stock market crash of 1929 forced Dillingham to give up producing. The writer Damon Runyon mentioned him in a short essay called ‘A Dog’s Best Friend’: “”Damon, what becomes of a man's friends when he gets sick?" I could not answer that one. It reminded me of a somewhat similar question asked by the once great theatrical producer, Charles Dillingham, at a time when he was broke and commencing to be forgotten along the big street, of which he was once one of the most glamorous and successful figures. He was sitting on a stool