Additionally, he owned and managed for many years the Cherry Lane Theatre in New York City – giving work to such future stars as Robert Walker Sr.,[1] Jennifer Jones[2] and Carl Reiner.

[4] His parents intended him to pursue a law career, but as a teenager Gilmore developed an interest in acting when he performed in amateur plays at Milwaukee's Grand Opera House, which was owned by his successful publisher father.

His clean-cut features, expressive brown eyes and shock of dark, wavy hair netted him many romantic roles, and his penchant for fine attire earned him a reputation as “the youngest, best-dressed leading man on the American stage.".

[12] When Gilmore's daughter, Regina, reached maturity, she joined her father in New York, adopted the stage name of Virginia, and assisted him in his theatrical work for the rest of his life.

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.

[18] 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.

Gilmore and Albert Plummer of Character Pictures began filming the South Seas adventure, The 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.

[23] Upon her death, the Gilmore estate, which was valued in excess of $1 million, was divided among relatives and the church, Catholic charities and Saint Raphael's Cathedral.