Beginning in 1883, Hoyt turned playwright and wrote a series of 20 farcical comedies (roughly one per year until his death) and a comic opera.

He was a highly popular playwright and producer, and was very financially successful, thanks in part to the assistance of his business partners, Charles W. Thomas and Frank McKee.

The occasion was an intimate affair of friends and close family due to the ill health of Hoyt's father.

Miskel, who was not considered to be in particularly strong health, died in October 1898,[7] at which point Hoyt went into a state of shock and drank excessive amounts of alcohol, "hoping to drown his sorrow".

[6] In the months following her death, Hoyt walked the streets and sat in hotel corridors, often being found asleep in public restrooms from exhaustion.

A year following Miskel's death, he attended the final rehearsals for what would be his last play A Dog in the Manger, which was poorly received by audiences and swiftly cancelled by his close friend and partner Frank McKee.

In the period leading up to his death, friends tried to appoint a guardian to act in his best interests if he were unable to care for himself, which raised outcry of a conspiracy to seize his property and gain control of his assets, believed to be worth around $300,000.

His former partner Frank McKee was one of his estate's executors, and the jewels went into his possession, despite claims from the mother and sister of his second wife Miskel that he had promised them the gems.