[3] In the early years of his career Olcott sang in minstrel shows, before studying singing in London during the 1880s.

[4] When the producer Augustus Pitou approached him in 1893 to succeed William J. Scanlan as the leading tenor in sentimental operettas on Irish themes, Olcott accepted and performed pseudo-Irish roles for the remainder of his career.

He wrote the complete scores to Irish musicals such as Sweet Inniscara (1897), A Romance of Athlone (1899), Garrett O'Magh (1901), and Old Limerick Town (1902).

For other productions he collaborated with Ernest R. Ball and George Graff in works such as The Irish Artist (1894), Barry of Ballymore (1910), Macushla (1912), and The Isle o' Dreams (1913).

[5] He was a good songwriter who captured the mood of his Irish-American audience by combining melodic and rhythmic phrases from traditional Irish music with melancholy sentiment.