O'Brien studied with Robert Prescott Stewart at the Royal Irish Academy of Music, where he was the first winner of the Coulson Scholarship (1888–90)[3] and frequently performed as both tenor singer, piano accompanist, and organist in many public concerts during the 1890s.
As a church musician, he became particularly involved in the Cecilian Movement, conducting works by Michael Haller and others, and also pursuing their artistic ideals in his own sacred choral compositions.
He was the founding conductor of the Dublin Oratorio Society (1906), the Brisan Opera Company (1916) and conducted at many ad hoc events.
As a much-demanded vocal coach he taught at his home, his best-known pupils including John McCormack, Margaret Burke Sheridan and James Joyce.
Before his work for the Palestrina Choir, O'Brien's musical interests were very broad, culminating in 1893 in the composition of the full-scale opera Hester.