He covered the Chicago World's Fair in 1893, the surrender of Sitting Bull, and the bloody Johnson County War in Wyoming.

[6] Hilliard was a close friend, from the early 1890s at the New York World, with American poet, novelist, and short story writer, Stephen Crane, who wrote The Red Badge of Courage.

The formal opening of the theater was highlighted by the performance of two plays produced and directed by Hilliard, The Thrice Promised Bride and The Queen's Enemies.

[8] In 1924, Hilliard was an actor in Ira Remsen's children's fantasy Mr. Bunt, where he played the role of Danny, a circus clown.

In 1925 he joined Thurston's magic show as an advance man and for the next 10 years toured America, meeting the most talented magicians of his day and recording their creations.