In 1881, in New York, she performed in Esmerelda, a play written by Frances Hodgson Burnett and William Gillette—this play would later become one of her most successful and popular performances. Notwithstanding, reviews for the play, and for Russell's performance, were becoming unfavourable by the ninth month of the play's run—the reviewer says of her performance: "If she cares for her future, she will not waste time in spoiling her voice. ...Lacking knowledge and training, she screams in a most unhappy fashion." It ran for a year at the Madison Square Theatre and had over two hundred showings.
After Esmerelda, Russell did not perform on a similar scale for a few years. However, she was not completely removed from theatrical life. In 1883 she joined the New York Fifth Avenue Theatre company, with her mother, Jane, and little brother, Tommy. She performed in one of the tour companies of the play Hazel Kirke, in the title role, before leaving to marry her first husband in 1884.
Russell shortly fell ill—the first reported illness of many throughout her career. She returned in 1885, playing Zaire in the play Broken Hearts written by W.S. Gilbert. Later in the year, she performed in Young Mrs. Winthrop with the Palmer Company in Philadelphia. She later returned to New York with the same company to perform at Madison Square Theatre as Ada in Sealed Intentions. which received a stellar review on opening night. She performed in Engaged as Maggie McFarland starting in 1886, where acclaim for her performances began to mount. A reviewer in the New York Times said she "Imparts the charm that belongs to her delicate beauty." Other performances in 1886 that Russell performed in with A.M. Palmer's company at Madison Square Theatre include Young Mrs. Winthrop as Edith Our Society and Love's Martyr.
In 1887, Annie Russell earned the title role in the play Elaine by George Parsons Lathrop and Harry Edwards, a play later adopted by Mr. Palmer's company. Also in 1887, she played the role of Sylvia in an adaptation of L'Monde ou l'on ennuie originally by Édouard Pailleron.
After a brief illness, Russell returned to the Madison Square Theatre company on a tour to San Francisco in 1888 in Partners. She continued to appear in more plays afterward including Captain Swift in 1889, This was her last role before an extended illness in 1890.
Russell remained with Mr. Palmer's company at the Madison Square Theatre until 1894, upon joining Charles Frohman's company, Empire Stock. She returned to the stage in 1894, playing the lead female part in The New Woman. She reprised her role in Esmerelda in 1894 as well. By 1895, Annie Russell appeared in an increasing number of plays. She performed in a new one-act play called Lethe, Later that year, she appeared in a prelude to Romeo and Juliet called Romeo's First Love and in The Gilded Fool which earned Russell more critical acclaim. Towards the end of the year, she took a new role in Senator and Ingenue as Ruth.
After an extended stay in Europe, Russell returned to the stage in Bret Harte's play Sue. She later reprised this role in London in 1898 at the Garrick Theatre. In the interim, she appeared in The Mysterious Mr. Bugle as Betty Fondacre, A Bachelor's Romance, Salt of the Earth, and Dangerfield '95 She performed many of her popular plays in London, including Sue and The Mysterious Mr. Bugle. She fell ill partway through 1899 and in June of that year returned to the United States to rest. She did, however, appear in a few plays, in 1899, Miss Hobbs with Ann Gilbert and 1900 in A Royal Family.
In 1902, Russell appeared in other plays with Ann Gilbert, in The Girl and the Judge. The play had great success, and ran from December 1901 to the fall of 1902. Subsequently, Russell starred in Mice and Men, still with Frohman's company. On December 30, 1902, Mrs. Roosevelt and other Washington dignitaries saw Russell perform in this play.
In 1903, Annie Russell performed in Boston, playing the title role in The Younger Mrs. Parling. She met her second husband, Oswald Yorke, in this play. Shortly after her marriage, Russell starred in a new play Brother Jacques.
Annie Russell returned to London in 1905. Her first play upon her return was the role Barbara Undershaft in Bernard Shaw's Major Barbara in that same year. She later returned to the United States, appearing in Friend Hannah in 1906. In the same year, she performed in Midsummer Night's Dream at the newly built Astor Theatre in Boston.
In 1908 she appeared with Robert Drouet in The Stronger Sex. Wagenhals & Kemper, owners of a company that Russell was a part of, bought land to build a $300,000 theatre bearing her name in New York City. It was described to be "state-of-the-art" In 1910 she joined the New Theatre Company, New York, appearing in Twelfth Night (1910), The Nigger (1909) She performed Twelfth Night in Washington for President Taft and the first Lady, Helen Taft. She appeared in a number of small plays, one under Charles Frohman's management, Gordon's Wife under Leibler Company until 1912 when she organized the Old English Comedy Company. They occupied The Princess Theatre in New York, a small theatre of 299 seats. A special feature of her new theatre company was that special matinées for schoolchildren on Fridays and Saturdays were performed, in addition to performances for private schools.
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