[1][2][3] Kyle's debuted as Guildenstern and the Second Grave Digger in Shakespeare's Hamlet at the Meyer's Opera House in Janesville, Wisconsin, on September 10, 1884.

He spent the following twelve seasons in tours with a number of large classical repertory companies and made his first appearance in New York in 1887 at the Windsor Theatre as Lucius in the James Sheridan Knowles play Virginius.

During the season of 1900/01 he played the title role in a successful tour of the Clyde Fitch romantic drama Nathan Hale, with co-star Nanette Comstock as Alice Adams.

Later in 1911 Kyle toured with the Coburn Players in classical repertory productions and in July of the following year with his own company played Malvolio in Shakespeare's comedy, Twelfth Night, at the Greek Theatre, Mt.

[1][2][4] Though Kyle would return to the stage many times over the following two decades, his last major Broadway role was probably Simeon in Louis Parker's 1913 pageant play, Joseph and His Brethren, which ran at the Century Theatre for 124 performances.

[7][8] Kyle married actress Amy Urcilla Hodges, a sister-in-law of the writer Louis Joseph Vance, at Fort Lee, New Jersey on June 28, 1915.

They had met at the Playhouse Theatre the previous year during a production of the Harvey O'Higgins and Harriet Ford story, Polygamy, in which Kyle played the Profit to Hodges’ Charlotte Marini.