[1] Born in Ireland and educated at Trinity College Dublin, Jessop began his career as a writer working for magazines in London before moving to California in 1873.
In 1882 Jessop began a prolific partnership with the dramatist William Gill with whom he co-authored several successful stage works; many of which were performed on Broadway, including In Paradise (1882), Facts, or His Little Hatchet (1883), A Bottle of Ink (1884), and Mam’zelle, or the Little Milliner (1885).
His later career as a writer in Europe was not prolific and was limited to the opera libretti for Charles Villiers Stanford's Shamus O'Brien (c. 1894) and Sidney Jones's My Lady Molly (1902), and two romance novels set in Ireland: Desmond O'Connor: the Romance of an Irish Soldier (originally published as a serialized novel in Munsey's Magazine in 1908; published as a book in 1914) and Where the Shamrock Grows: The Fortunes and Misfortunes of an Irish Family (1911).
[6] His third play, Sam'l of Posen; or, The Commercial Drummer, was his greatest achievement as a playwright and had a successful national tour that included a twelve-week long run on Broadway in 1881.
[5] Jessop's Sam’l of Posen was followed by another commercially successful play, In Paradise (1882) which he co-authored with dramatist William Gill as a starring vehicle for the actor John T.
Other stops on the tour included performances at the Park Theatre, Brooklyn, Grand Opera House, St. Louis, and the McVicker's Theater in Chicago among other venues.
[12] This second play was tremendously profitable and became the greatest success for the Florences in their acting careers; remaining in their regularly performed repertoire for the next six years including multiple runs at Broadway theatres.
[13] Along with Fred Maeder and Clay Greene, Jessop was one of several writers who contributed to modifications made to Gill's hit musical My Sweetheart after it premiered in 1881.
[14] The work turned the actress Minnie Palmer into an international star; and had a lengthy run in London's West End in addition to spending years touring the United States, Europe, and Australia in the 1880s, 1890s, and the 1900s.
The work was a stage adaptation of Charles Reade's 1884 novel Single Heart and Double Face and was skewered in reviews from the New York press.
[18] They rebounded later that year with a popular if not critical success, writing the libretto for the musical A Bottle of Ink (1884 premiere in Boston; 1885, Comedy Theater, Broadway), which starred soprano Ida Mülle, the comic actor Jefferson De Angelis, and the actress Hattie Starr.
This work premiered on 5 September 1884 in Kingston, New York and toured to Syracuse, Buffalo, Rochester, and Brooklyn before finally settling in for a successful run at Broadway's Fifth Avenue Theater.
[21] In reality, the work contained a significant portion of material authored by Gill earlier for his 1884 musical flop Two Bad Men which he had created in collaboration with the composer Gustave Kerker for the American stage.
[23] A planned new work by the Gill and Jessop creative team for the actress Leonora Bradley was supposed to premiere in London in the summer of 1887 but was abandoned and never materialized.
[24] In 1891 he inherited the Marlfield estate in County Dublin after the death of his cousin Catherine Jessop, and it is likely that his return to Europe occurred as a result of this event.