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. When between performances on stage, like many performers, he worked odd jobs to earn money: as a
printer,
barber, boxing trainer, and railroad
porter. In 1903, he joined
Hamilton, Ontario's Canadian
Jubilee Singers. In 1905, he started performing with traveling musical troupes of the
Red Cross and the Candy Shop of America. He also played his first dramatic roles and honed his character acting in Chicago. He performed with
Robert T. Motts'
Pekin Theater in Chicago for four years until 1911. Soon after, he toured the United States with the
Pan-American Octetts. Gilpin worked with
Rogers and Creamer's
Old Man's Boy Company in New York. In 1915, Gilpin joined the
Anita Bush Players, led by Anita Bush, as they moved from the
Lincoln Theater in
Harlem to the
Lafayette Theatre. As New York theater was expanding, this was a time when the theatrical careers of many famous black actors were launched. In 1916, Gilpin made a memorable appearance in whiteface as
Jacob McCloskey, a slave owner and villain of
Dion Boucicault's
The Octoroon. Though Gilpin left Bush's company over a salary dispute, his reputation allowed him to get the role of Rev. William Curtis in the 1919 premier of
John Drinkwater's Abraham Lincoln. Gilpin's
Broadway debut led to his being cast in the premier of
Eugene O'Neill's
The Emperor Jones. He played the lead role of Brutus Jones to great critical acclaim, including a lauded review by writer
Hubert Harrison in
Negro World. Gilpin's achievement resulted in
The Drama League's naming him as one of the 10 people in 1920 who had done the most for American theater. He was the first black American so honored. Following the Drama League's refusal to rescind the invitation, Gilpin refused to decline it. When the League invited Gilpin to their presentation dinner, some people found it controversial. At the dinner, he was given a standing ovation of unusual length when he accepted his award. 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 wanted O'Neill to remove the word "nigger", which occurred frequently in the play. The playwright refused, asserting its use was consistent with his dramatic intentions. In 1921, Gilpin was awarded the
NAACP's
Spingarn Medal. He was also honored at the
White House by President
Warren G. Harding. A year later, the
Dumas Dramatic Club (now the
Karamu Players) of
Cleveland renamed itself the Gilpin Players in his honor. When they could not come to a reconciliation, O'Neill replaced Gilpin with
Paul Robeson as Brutus Jones in the London production. In early April 1922, Gilpin became one of the first black performers to give a dramatic presentation on radio. He gave readings from "The Emperor Jones" over greater Boston station
WGI, from their Medford Hillside studios. After the extended controversy and the disappointment of losing his signature role, Gilpin started drinking heavily. He never again performed on Broadway. He died in 1930 in
Eldridge Park, New Jersey, his career in shambles. He was buried in an unmarked grave in
Woodlawn Cemetery in the
Bronx, his funeral arranged by friends shortly after his death. In 1991, 61 years after his death, Gilpin was inducted into the
American Theater Hall of Fame. ==Relationship with Eugene O'Neill==