His most critically acclaimed work is "The Praise of Ben Dorain," but he is well known for his poetic commentaries on contemporary events. In the Jacobite rising of 1745 which attempted to return the House of Stuart to the throne of Scotland and England, Duncan fought on the Hanoverian side and composed a humorous song after losing his borrowed sword at the battle of Falkirk in January 1746. Following that uprising, however, he composed a best selling poem attacking the portion of the Act of Proscription outlawing the wearing of highland dress and was briefly imprisoned., When the ban against the wearing of the kilt was repealed, he celebrated with another poem, entitled "Orain na Briogas " or "Song of the Breeches."