Folk song researcher Donal O'Sullivan has written that Captain Edmund O'Ryan's, "gay chivalry, daring exploits, and 'moving accidents by flood and field' would indeed make fine material for a historical novel.
"[2] According to James Clarence Mangan, O'Ryan was born in Shanbohy, in the civil parish of Templebeg (Irish: An Teampall Beag), in the half-barony of Kilnamanagh Upper in Tipperary, "previous to the wars of 1690".
[6] His father's family was descended from the derbhfine of the last Chief of the Name of Clan O'Ryan and Lord of Kilnalongurty; but his ancestors had lost their ancestral lands fighting for the Hiberno-Norman Fitzgerald dynasty during the Elizabethan era Desmond Rebellions.
[9] A further background to Captain O'Ryan's career was the confiscation of Royalist-owned land after the Cromwellian conquest of Ireland in the Act of Settlement 1652, upon which when many similarly dispossessed Cavaliers also became outlaws, known as "tories" or "rapparees".
O'Ryan also accompanied Patrick Sarsfield and Galloping Hogan during the raid that resulted in the destruction of the William of Orange's siege train at Ballyneety.
[13] Author and poet Robert Dwyer Joyce would later dub Edmund O'Ryan, "one of the noblest gentlemen and bravest Rapparee captains that ever drew sword or shook bridle free in the cause of worthless, war-minded King James the Second.
Some of the most gallant and intrepid remained behind to carry on an independent fight by every means in their power: constantly raiding the encampments of the English soldiery, harassing its lines of communication, and retreating into their hideouts in the hills, each man of them with a price in his head.
"[16] Along with fellow raparees Colonel John Hurley, Colonel Dermot Leary, Captain Matthew Higgins and John Murphy, O'Ryan issued a proclamation in December 1694, denouncing all those disloyal to King James II, offered a reward of £200 to anyone who brought to them any member of William of Orange's privy council and a further bounty of £50 to anyone who delivered to them a military officer still in arms against the House of Stuart.
Upon bringing the severed head to the county seat of Cashel (Irish: Caiseal), however, Dwyer learned to his chagrin that O'Ryan had been pardoned two days previously and that no reward would be given.
In 1963, Matthew Ryan, a relative of the outlaw and retired officer in the United States Navy, erected a tombstone: The song is usually sung in Irish, but various English versions are popular as well.