presented an English fairy play, Little Red Riding Hood, in January 1900. Jackson was 'Riding Hood', with Madge Lessing as 'Little Boy Blue' and Kitty Mitchell as 'Little Jack Horner'. The production was the work of Edward E. Rice. In 1901, Jackson created the title role in Miss Bob White, a comic opera written by Willard Spenser. The story tells of two millionaires compelled to live for several months as tramps after losing an election bet. They come to a dairy farm close to Philadelphia and are put to work. Jackson is a New York society belle who arrives at the farm disguised as a dairy maid. She successfully woos the man she is infatuated with. In February 1905 she was in a production of The Brixton Burglary at the Carnegie Lyceum in Manhattan. Written by Frederick W. Sidney, the presentation could not be staged in Brooklyn, New York, because of the burning of the Brooklyn Academy of Music. Several hundred members and friends of the Amaranth, Brooklyn's oldest dramatic society, attended the performance. She starred in The Blue Moon on Broadway in 1906. Henry W. Savage secured Jackson to sing the role of Sonia in the original Broadway production of The Merry Widow. The Viennese comic opera was written by Victor Leon, Franz Lehár and Leo Stern. The production opened first in Syracuse, New York, on September 24, 1907. The three-act opera played the New Amsterdam Theatre for the first time on October 21. Jackson fainted twice during a Saturday matinee in March 1908. Her illness brought about her replacement by Lois Ewell. She fainted again while leaving the stage at the close of the second act on March 17. After being revived by a doctor, Jackson resumed her role at the beginning of the third act. The audience enthusiastically applauded her for her determination. She attributed her fainting spells to a weak heart caused by grippe, which she suffered from during the previous winter. In January 1914, Jackson debuted as a vaudeville performer at the Orpheum Theatre in Brooklyn, New York. The venue was run by B.F. Keith. In February 1915 she appeared in A Pair of Sixes with Ralph Herz at the Belasco Theatre in Washington, D.C. The play dealt with two pillmakers who disagreed on how to conduct their business. Marriages Jackson married J. Fred Zimmerman Jr., business manager of the Chestnut Street Theater, in 1902