Rolleston was born in Glasshouse, Shinrone, County Offaly, the son of a judge.

After a time in the German Empire he founded the Dublin University Review in 1885; he published Poems and Ballads of Young Ireland (1888), and a Life of Lessing (1889).

[2] In London in the 1890s he was one of the Rhymers' Club and a founder-member of the Irish Literary Society.

He was to cross paths several times, and sometimes to clash, with W. B. Yeats, who described Rolleston in his memoirs as an "intimate enemy".

He also spent time as a journalist, and as a civil servant involved with agriculture.