Born in Bellaghy, County Derry Oliver grew up in a musical setting. His father James played and taught both the tin whistle and accordion.

Oliver started his musical career playing the fiddle with local groups throughout Derry. At eighteen, Oliver went to Tenerife in the Canary Islands where he spent the next few years playing in Paddy's Irish Pub. After leaving Tenerife, Oliver came to America where his brother Barney was playing with the popular Irish group the Bards.

Oliver has played coast to coast in many cities including: St. Louis, Seattle, Chicago, Savanna, Atlanta, Boston, and Philadelphia. He served as the general manager of the Blarney Stone Pub and Restaurant in St. Louis from 1986 to 1990.

Oliver has opened for Ralph Mactell, Christy Moore, Tommy Makem, and the Clancy Brothers. He now resides in the Irish enclave of Upper Darby just outside Philadelphia. He has become a favorite at Brittingham's, Kildare's, and many other Irish Pubs.