Middle Career
Gilmore reached full star status in late 1900 with his performance in The Dawn of Freedom at the Fourteenth Street Theatre in New York City. He performed relentlessly all over the country in scores of plays, often in roles that portrayed him as a swashbuckling lover. Audiences flocked to see him in productions such as Captain Debonnaire, The Mummy and the Hummingbird and The Boys of Company B.
Gilmore married Mary A. Goodwin in 1901 and was divorced from her in January 1909. In November of that year, he married actress Ethel Elizabeth Cauley, while on tour in Staunton, Virginia.
In addition to operating his own touring stage company and acting in productions throughout the United States, Gilmore began making feature films in 1915. By 1920, he had starred or had major roles in nine movies and accumulated more than $225,000 in cash and tangible assets, including 40 acres (160,000 m2) of land on Anna Maria Island in Florida. It was here that he hoped to build a movie colony – Paul Gilmore’s Oriental Film City – that would rival Hollywood. He and his fourth wife, Pickett Gilmore, were principal officers in the company.
Gilmore and Albert Plummer of Character Pictures began filming the South Seas adventure, Isle of Destiny, in the spring of 1920, on Anna Maria Island. Gilmore pumped huge amounts of his own cash into the production, footing the bill for the importation by boat (there was no serviceable road or bridge to the island) of cars, horses and some 200 actors.
Isle of Destiny, a six-reeler, performed well when it premiered in New York theaters, and Gilmore planned at least two other films for production on Anna Maria Island. But his speculations in real estate failed, and Gilmore lost all his assets and most of his cash. He returned to New York City where he settled in Greenwich Village over a tobacco warehouse that he would transform into the Paul Gilmore Cherry Lane Theatre. Divorced from his fourth wife by the 1930s, he was joined in New York by his daughter, and together they ran the small venue and starred in many of its productions.
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