He soon established himself as a solo artist and found his greatest success singing traditional Irish music, both old and contemporary.
[3] After finishing secondary school in 1990, he played the local scene with a couple of bands, but it was his meeting with composer Phil Coulter in Westport, County Mayo, that changed his career.
Within a few short months of this meeting, he appeared at the Cork Opera House, and the National Concert Hall in Dublin.
[3] With De Dannan, Fleming's voice was brought to Australia, China, Hong Kong, and, once again, the United States.
This building has a capacity of 5,000 and had been host to Holy Mass celebrated by Pope John Paul II on his visit to Ireland in September 1979.
PBS began broadcasting the recording of the concert under the title Voice of Hope in the United States in August 2005.
[8] In 2007, Fleming recorded his new live show, A Journey Home, at Ireland's National Events Centre in Killarney to an audience of 2,000.
[9] He participated in season 4 of Celebrity Bainisteoir in 2011, managing St Patrick's GAA Club Dromard, Sligo.
[10] In November 2014, Fleming participated in the inaugural cruise of the Australian performing arts on the MS Radiance of the Seas along with, among others, Cheryl Barker, David Hobson, Colin Lane, Teddy Tahu Rhodes, Simon Tedeschi, Elaine Paige, Marina Prior, and Jonathon Welch.