Dolan's first US tour was in 1965 and followed an offer, which he refused, to play in Las Vegas. Instead, he decided to play a whistle-stop tour of Irish-American venues in places such as Chicago, New York and Boston. An added benefit to this string of engagements was the opportunity to hear American music which hadn't yet been played in the UK and Ireland. The first song gleaned in this fashion was the Jim Reeves song, "(That's When I see the Blue in Your) Pretty Brown Eyes" which Dolan released on the Pye label in 1966.