A native of Ballyvourney, a small village in the heart of the Muskerry Gaeltacht (an Irish speaking area) in County Cork, Jim Flanagan now lives in Hattiesburg, Mississippi. He has performed at major festivals (Milwaukee, Dallas, Colorado, Atlanta, New Orleans, Savannah, Austin, Jackson) and in regular pub performances over the years has established himself as a significant force in Irish music in the Southeastern United States. Steve Winick (Dirty Linen) compares him favorably to Daithi Sproule (of Altan) and the great traditional singer Joe Heaney (Seosamh Ó hÉanaí) - in whose company any Irish singer would be proud to be placed.

Ballyvourney is an area long recognized as a center of poetry, music, and dance. It is the birthplace of many highly respected poets and musicians, among these the famous poet Seán Ó Riordáin. Many great Irish musicians have lived in the area, including Seán Ó Riada, Jackie Daly, John Connell, and the great source singer Elisabeth Cronin. Flanagan draws on this wellspring of tradition with pride of place in his stage performances. He provides a mix of both Irish language and English language songs; songs based in the old style (sean nós) tradition as well as contemporary ballads, many of which lend themselves well to audience participation. His performances are interwoven with his compelling Irish humor, the stories of Ireland and his memories of home, leaving one with a feeling of having been entertained and enriched as well.