[citation needed] Howard is the creator of the "rugby jock" character Ross O'Carroll-Kelly, whose exploits have been the subject of twenty-one novels and three other books that have sold over 1.5 million copies in Ireland.
He was named National Newspapers of Ireland Columnist of the Year in 2013 for his weekly column in The Irish Times on Saturday written under the Ross O'Carroll-Kelly pseudonym.
His first non-Ross-related venture into fiction: Triggs – The Autobiography of Roy Keane's Dog – was a #1 Bestseller in 2012, and short-listed for an Irish Book Award.
Howard is a record five-time Irish Book Award winner, collecting the Best Popular Fiction prize in 2007 for Should Have Got Off at Sydney Parade, in 2010 for The Oh My God Delusion, in 2013 for Downturn Abbey (each parts of the Ross O'Carroll-Kelly series), Non-Fiction Book of the Year in 2016 for the biography of Tara Browne, "I Read the News Today, Oh Boy" and a Special Recognition Award for his contribution to the Irish publishing industry in 2024.
In September 2019, he was the subject of an hour long RTÉ documentary entitled “We Need to Talk about Ross” produced by Adrian McCarthy of Wildfire Films.