The second son of John Cunningham and Elizabeth Harley, daughter of a Dumfries merchant, he was born at Culfaud, Kirkcudbrightshire, on 25 June 1776.
[1][2] At sixteen Cunningham became clerk to John Maxwell of Terraughty, but remained with him only a short time.
While at Cambridge he wrote: The Hills o' Gallowa, wrongly included in a collected edition of Robert Burns published by Orphoot at Edinburgh in 1820; a satirical poem entitled The Cambridgeshire Garland; and another that was similar, The Unco Grave.
[1] In 1806 Cunningham began to contribute poetry to the Scots Magazine, his verse being mainly on Lowland country life.
On the founding of the Edinburgh Magazine in 1817, he contributed to it poems and songs, and under the title Literary Legacy, prose sketches on society, stories and antiquarian topics.