In addition to a solo career and as a member of Planxty, O'Flynn recorded with: Christy Moore, Dónal Lunny, Andy Irvine, Kate Bush, Mark Knopfler, The Everly Brothers, Emmylou Harris, Mike Oldfield, Mary Black, Enya and Sinéad O'Connor.

In 1972, O'Flynn co-founded the Irish traditional music group Planxty,[3] alongside Christy Moore, Andy Irvine and Dónal Lunny and remained a member throughout the band's various incarnations.

While Seán Ó Riada and The Chieftains had reinvigorated Irish traditional instrumental music in an ensemble format during the 1960s, Planxty built on that foundation and took it one step further.

As O'Flynn grew in his skill as a musician and as he began to meet pipers like Willie Clancy and Séamus Ennis, he became acutely aware of his position in the tradition of piping.

[4]Following the break-up of Planxty in 1983, O'Flynn found work as a session musician with such prominent artists as The Everly Brothers, Enya, Kate Bush, Nigel Kennedy, Rita Connolly, and Mark Knopfler.

Awardees include Úna Monaghan,[6] Barry Kerr,[7] Jack Talty,[8] Louise Mulcahy[9] and Strange Boy (aka Jordan Kelly).