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After the success of "Tillie's Nightmare," life was not so easy for the actress. In the meantime, World War I had begun and Dressler worked tirelessly selling Liberty Bonds. When the war ended, so did Dressler's Broadway career. By this time she was nearly fifty years old. She had to care for James Dalton, an invalid, until his death. No acting offers came her way. Producers and managers were embarrassed when they met her. Her funds ran out. She had to sell a little farm in New Hampshire that she had bought for her retirement. In spite of her adversities, Dressler's daring spirit prevailed. She moved to the Ritz Hotel in New York where an old friend, Albert Keller, the manager, let her a room at a very low rate. Later she accepted the position as hostess for the Ritz Supper Club.

For seven years Dressler lived at the Ritz showing a smiling face to the world, but lamenting privately the lack of career opportunities. If she had reflected upon her life, she would have found much of which to be proud. Not only had she been daring enough to choose a stage career, but also had been successful enough to have earned a thousand dollars a week on the vaudeville stage. Besides becoming a well-paid performer, she had been acclaimed by those of high social standing including Mrs. Styvesant Fish of New York's elite "400," King George the Fifth, and American president, F.D. Roosevelt. Despite this adulation, Dressler was not satisfied to end her life in show business, nor did she have the funds to retire. She longed to get back on the stage where she had entertained thousands with her broad and robust comedy. One would have some difficulty imagining that this trouper would resurface in the entertainment world, and that millions of fans would follow her career in the newest direction - talking pictures.