Jeannie Robertson sang The Gypsy Laddies, in a recording made in 1955 where she is accompanied by Josh MacRae on guitar, on her 1957 Riverside album Songs of a Scots Tinker Lady. Another recording made by Bill Leader in 1959 was released on her eponymous Topic album Jeannie Robertson. Hamish Henderson noted on both albums:

This classic ballad—no. 200 in the great Child collection—is widely known throughout the British Isles and America. In Scotland, the ballad is often associated with the Ayrshire house of Cassilis, and is declared to be a “true” ballad, although history does not bear this out. However, the ballad tale, in which handsome gipsies beguile a noble lady by the sweetness of their singing, has naturally made it very popular with the Scots travelling folk.