In 1920, he was the first black person to receive The Drama League's annual award as one of ten people who had done the most that year for American theatre.
[2] In 1896 at the age of 18, Gilpin joined a minstrel show, leaving Richmond and beginning a life on the road that lasted for many years.
In 1916, Gilpin made a memorable appearance in whiteface as Jacob McCloskey, a slave owner and villain of Dion Boucicault's The Octoroon.
He played the lead role of Brutus Jones to great critical acclaim, including a lauded review by writer Hubert Harrison in Negro World.
[7] Although Gilpin continued to perform the role of Brutus Jones in the U.S. tour that followed the Broadway closing of the play, he had a falling-out with O'Neill.
Gilpin was the first actor to play the role of Emperor Jones when it was first staged on November 1, 1920, by the Provincetown Players at the Playwright's Theater in New York City.
[15] Gilpin wanted O'Neill to remove the word "nigger" from the play altogether, which occurred frequently in the play, but the playwright refused, arguing its use was consistent with his dramatic intentions and that the use of language was, in fact, based on a friend, an African-American tavern-keeper on the New London waterfront that was O'Neill's favorite drinking spot in his home town.
[citation needed] When they could not come to a reconciliation, O'Neill replaced the middle-aged Gilpin with the much younger and then unknown Paul Robeson, who had only performed on the concert stage.
[17] He received excellent reviews and, coupled with his performance in the 1928 London production of the musical Show Boat, went on to worldwide fame as one of the great artists of the 20th century.
[19] The production, which ran for 61 performances, is remembered today for the acting debut of a young Moss Hart as Smithers and broke social barriers and defied conventions of the day as the first American play to feature an African-American central character portrayed in a serious manner.
[20] The play was adapted for a 1933 feature film starring Paul Robeson, directed by Dudley Murphy, an avant-garde filmmaker of O'Neill's Greenwich Village circle who pursued the reluctant playwright for a decade before getting the rights from him.
[citation needed] Gilpin continued to make a small living performing monologues from O'Neill's play at church gatherings, but after the extended controversy and the disappointment of losing his signature role, succumbed to depression and began drinking heavily.
[citation needed] He was buried in an unmarked grave in Woodlawn Cemetery in the Bronx, his funeral arranged by friends shortly after his death.