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His popularity began on BBC Radio Ulster in 1991 when he began writing and broadcasting humorous monologues as The Bard of Tyrone on the Just Jones show. Over a period of six years he wrote and performed over 200 poems. As a direct result of this he was asked to appear at the Belfast Festival at Queens University Belfast (QUB) and on the BBC Radio Ulster programme, Laugh a Minute.
Caulfield became one of the busiest warm up men for both BBC and UTV on shows such as"The Kelly Show" Get it Right Next Time, Town Challenge, The Daniel O'Donnell Show, Give my Head Peace, Saints and Scholars, Scots Irish Evenings and The 11+ Show.
He has appeared on The Gerry Kelly Show, McKeever Show and All Mixed Up for UTV and Pass it On, Town Challenge and The Big Science Quiz for the BBC. He interviewed Jade Goody for Channel 4 in What Jade Did Next. T.V credits in his own shows include An Evening with James Young and a four part series Our William both on BBC 1 NI.
Caulfield is well established in theatre playing Nathan Detroit in Guys and Dolls, Henry Higgins in My Fair Lady, Ebenezer Scrooge in A Christmas Carol and Frank in Annie Get Your Gun, all for Enniskillen's Light Operatic Society. Other stage roles include Look Who's Talking, Da and Playboy of the Western World.
He has appeared in Pantomime in Belfast in the Waterfront Hall (2001–2003), Grand Opera House (2004–2005) and returns now each year to Derry in the Millennium Forum since 2006.